Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2011 Mar 9;111(3):1417-92.
doi: 10.1021/cr100327p. Epub 2011 Feb 14.

Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners

Ranjan Jana  1 , Tejas P Pathak, Matthew S Sigman
Affiliations
Review

Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners

Ranjan Jana et al. Chem Rev. .
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Cross-Coupling of C(sp3)-Organometallics
Figure 2
Figure 2
Standard Methods of Preparation for Alkylzincs Reagents
Figure 3
Figure 3
α-Amino Acid-Derived Alkylzinc Reagents (Jackson and coworkers, 1998)
Figure 4
Figure 4
Decomposition of Amino Acid Derived Alkylzinc Reagents (Jackson and coworkers, 2008)
Figure 5
Figure 5
Synthesis of Symmetrical 2,5-dialkyl Benzoquinones via Negishi Coupling (Bäckvall and coworkers, 1998).
Figure 6
Figure 6
Negishi Coupling of Ethyl 3-bromo-3,3-difluoropropionate (Qing and coworkers, 2000)
Figure 7
Figure 7
Negishi Coupling of Unsaturated Organotellurium Compounds (Dabdoub, and coworkers, 2000)
Figure 8
Figure 8
Negishi Coupling of Cyclic α-Iodoenones (Negishi and coworkers, 2000)
Figure 9
Figure 9
Regioselective Negishi Coupling of 2,4-Dibromothiazoles (Bach and coworkers, 2002)
Figure 10
Figure 10
Stereoselective Negishi Couplings (Negishi and coworkers, 2004)
Figure 11
Figure 11
Negishi Coupling of Dihaloalkenes (Wnuk and coworkers, 2006) aisolated yields were based on E-isomer only.
Figure 12
Figure 12
High TON in Pd(0)-Catalyzed Negishi Couplings (Doucet and coworkers, 2006)
Figure 13
Figure 13
Negishi Coupling of Alkenyl Phosphates: (Skrydstrup and coworkers, 2007)
Figure 14
Figure 14
Negishi Coupling using π-Acceptor Ligands (Lei and coworkers, 2007)
Figure 15
Figure 15
Negishi Coupling of 5-iodo-pyrimidine Nucleosides (Kung and coworkers, 2008)
Figure 16
Figure 16
Pd-phosphinous Acid-Catalyzed Negishi Couplings (Wolf and coworkers, 2008)
Figure 17
Figure 17
Negishi Coupling of Aryl Halides Bearing Acidic Protons (Knochel and coworkers, 2008)
Figure 18
Figure 18
Pd-nanoparticle-catalyzed Negishi couplings (Lei and coworkers, 2008)
Figure 19
Figure 19
Negishi Coupling of Secondary Alkylzinc Halides (Buchwald and coworkers, 2009)
Figure 20
Figure 20
Negishi Coupling of Thiomethyl-substituted Heterocycles (Knochel and coworkers, 2009)
Figure 21
Figure 21
Negishi Couplings in Aqueous Medium (Lipshutz and coworkers, 2009)
Figure 22
Figure 22
Negishi Coupling with Unactivated Alkyl Halides and Tosylates (Fu and coworkers, 2003)
Figure 23
Figure 23
Alkyl-Alkyl Negishi Coupling using NHC-ligands (Organ and coworkers, 2005)
Figure 24
Figure 24
Oxidative C(sp3)-C(sp3) Coupling (Sigman and coworkers, 2009)
Figure 25
Figure 25
Oxidative Cross-Coupling through Double Transmetalation (Lei and coworkers, 2006)
Figure 26
Figure 26
Oxidative Cross-Coupling with Terminal Alkynes (Lei and coworkers, 2010)
Figure 27
Figure 27
Formation of Ketones via Negishi Coupling (Ohno and coworkers, 2009)
Figure 28
Figure 28
Negishi Coupling of Thioglycolic Acids (Liebeskind and coworkers, 1999)
Figure 29
Figure 29
Negishi Coupling of 4-diethylphosphonooxycoumarins (Yang and coworkers, 2001)
Figure 30
Figure 30
Negishi Coupling of Amino-heteroaryl Chlorides (Walters, 2005)
Figure 31
Figure 31
Ni-Catalyzed Three-Component Coupling (Terao and coworkers, 2009)
Figure 32
Figure 32
Alkylative Carboxylation of Alkynes (Mori and coworkers, 2001)
Figure 33
Figure 33
Carboxylation of Alkylzinc Reagents (Oshima and coworkers, 2008)
Figure 34
Figure 34
Substrate-Controlled Alkyl-Alkyl Negishi Coupling (Knochel and coworkers, 1996)
Figure 35
Figure 35
Ni-Catalyzed Alkyl-Alkyl Negishi Couplings (Knochel and coworkers, 1998)
Figure 36
Figure 36
Ni-Catalyzed Alkyl-Alkyl Negishi Couplings (Knochel and coworkers, 2002)
Figure 37
Figure 37
Negishi Coupling of Secondary Alkyl Halides (Fu and coworkers, 2003)
Figure 38
Figure 38
1,3,8,10-Tetraenes in Negishi Coupling (Kambe and coworkers, 2004)
Figure 39
Figure 39
C1-Alkylation of Glycosides (Gagné and coworkers, 2007)
Figure 40
Figure 40
Ni-Catalyzed Radical Cyclization (Cárdenas and coworkers, 2007)
Figure 41
Figure 41
Secondary-Secondary Negishi Couplings (Fu and coworkers, 2008)
Figure 42
Figure 42
Various Organoboron Reagents
Figure 43
Figure 43
Preparation of Common Alkylboron Reagents
Figure 44
Figure 44
Rate-Dependence on Boron Derivatives (Soderquist and coworkers, 1998)
Figure 45
Figure 45
Suzuki-Miyaura Coupling on Amino Acid Synthons (Taylor and coworkers, 1999)
Figure 46
Figure 46
Suzuki-Miyaura Coupling on Amino Acid Synthons (Johnson and coworkers, 2000)
Figure 47
Figure 47
Cross-Coupling with N-Boc-4-methylene Piperidines (Vice and coworkers, 2001)
Figure 48
Figure 48
Suzuki Coupling on C1-iodo-glycals (Tan and coworkers, 2004)
Figure 49
Figure 49
Suzuki Coupling for Selective Monoalkylations (Roulland and coworkers, 2007)
Figure 50
Figure 50
Suzuki Coupling for the Synthesis of Trisubstituted Olefins (Roulland and coworkers, 2007)
Figure 51
Figure 51
Suzuki Coupling in Carbapenem Analog Synthesis (Narukawa and coworkers, 1997)
Figure 52
Figure 52
Suzuki Coupling in Polyether Synthesis (Sasaki and coworkers, 1998)
Figure 53
Figure 53
Suzuki Coupling with Arenediazonium o-benzenesulfonamides (Dughera and coworkers, 2008)
Figure 54
Figure 54
Formation of Six-Membered Rings with Exocyclic Double Bonds (Soderquist and coworkers, 1995)
Figure 55
Figure 55
Carbonylative Suzuki-Miyaura Couplings
Figure 56
Figure 56
Radical Oxidative Addition (Suzuki and coworkers, 1992)
Figure 57
Figure 57
Alkyl-Alkyl Suzuki-Miyaura Couplings with Alkyl Bromides (Fu and coworkers, 2001)
Figure 58
Figure 58
Alkyl-Alkyl Suzuki-Miyaura Couplings with Alkyl Chlorides (Fu and coworkers, 2002)
Figure 59
Figure 59
Alkyl-Alkyl Suzuki Couplings with Alkyl Tosylates (Fu and coworkers, 2002)
Figure 60
Figure 60
Alkyl-alkyl Suzuki-Miyaura Couplings with Alkyl Halides (Capretta and coworkers, 2004)
Figure 61
Figure 61
Alkyl-Alkyl Suzuki Coupling with Alkyl Iodides (Caddick and coworkers, 2004)
Figure 62
Figure 62
Alkyl-alkyl Suzuki couplings with alkyl halides (Organ and coworkers, 2008)
Figure 63
Figure 63
Alkyl-Alkyl Suzuki-Miyaura Couplings with Secondary Alkyl Bromides (Fu and coworkers, 2007)
Figure 64
Figure 64
Formation of Ketones from Thioesters (Liebeskind and coworkers, 2004)
Figure 65
Figure 65
Formation of Amides from Carbamoyl Chlorides (Takemoto and coworkers, 2007)
Figure 66
Figure 66
Suzuki-Miyaura Coupling of Alkylboronic Acids (Falck and coworkers, 2001)
Figure 67
Figure 67
Suzuki Coupling of Phenethylboronic Acids (Molander and coworkers, 2002)
Figure 68
Figure 68
Suzuki Coupling with Aryl Halides (Hartwig and coworkers, 2002)
Figure 69
Figure 69
Suzuki Coupling with Phosphite Ligands (Bedford and coworkers, 2003)
Figure 70
Figure 70
Suzuki Coupling in Aqueous Medium (Nájera and coworkers, 2004)
Figure 71
Figure 71
Suzuki Coupling with Tedicyp Ligand (Doucet and coworkers, 2004)
Figure 72
Figure 72
Pd Nanoparticle-Catalyzed Suzuki Couplings (Ranu and coworkers, 2009)
Figure 73
Figure 73
Alkyl-Alkyl Suzuki Couplings with Alkylboronic Acids (Fu and coworkers, 2002)
Figure 74
Figure 74
Suzuki Coupling with Substituted Cyclopropylboronic Acids.
Figure 75
Figure 75
Suzuki Coupling with Alkylboronic Esters (Suzuki and coworkers, 1989)
Figure 76
Figure 76
Suzuki Coupling with Cyclopropylboronic Esters (Marsden and coworkers, 1996)
Figure 77
Figure 77
Suzuki Coupling with Cyclopropylboronic Esters (Charette and coworkers, 1997)
Figure 78
Figure 78
Suzuki Coupling with Catecholboranes (Andrus and coworkers, 2001)
Figure 79
Figure 79
Suzuki Coupling with Alkyl Potassium Trifluoroborates (Molander and coworkers, 2001)
Figure 80
Figure 80
Suzuki Coupling with Potassium Trifluoroborates (Deng and coworkers, 2004)
Figure 81
Figure 81
Suzuki Coupling with Substituted Cyclopropyl Potassiumtrifluoroborates (Charette and coworkers, 2005)
Figure 82
Figure 82
Suzuki Coupling with Potassium Trifluoroboratohomoenolates (Molander and coworkers, 2008)
Figure 83
Figure 83
Suzuki Coupling with Secondary Potassiumtrifluoroborates (Molander and coworkers, 2008)
Figure 84
Figure 84
Seminal Report (Corriu and Masse, 1972)
Figure 85
Figure 85
Seminal report (Kumada and coworkers, 1972)
Figure 86
Figure 86
a) Mechanistic Studies, b) Proposed Mechanism
Figure 87
Figure 87
Cross-Coupling of Aryl and Alkenyl Halides (Kumada and coworkers, 1976)
Figure 88
Figure 88
Cross-Coupling of β-bromovinylethers (Kumada and coworkers, 1976)
Figure 89
Figure 89
Trialkylation of Trichlorobenzenes (Tamborski and coworkers, 1983)
Figure 90
Figure 90
Synthesis of Multi-substituted 1,3-Butadienes (Shi and Shao, 2005)
Figure 91
Figure 91
Alkylation of Organosulfides (Takei and coworkers, 1979)
Figure 92
Figure 92
Scope and Proposed Mechanism (Takei and coworkers, 1979)
Figure 93
Figure 93
Synthesis of Substituted Purines (Takei and coworkers, 1985)
Figure 94
Figure 94
Cross-Coupling of Thioaryls with Grignard reagents (Wenkert and coworkers, 1985)
Figure 95
Figure 95
Cross-Coupling of Sulfides with Alkyl Grignards (Oshima and coworkers, 2008)
Figure 96
Figure 96
Cross-Coupling of Vinyl Triflates (Fiaschisi and coworkers, 1999)
Figure 97
Figure 97
Effect of Ligand Bite Angle on Product Distribution
Figure 98
Figure 98
Synthesis of Substituted Dienes (Bäckvall and coworkers, 1999)
Figure 99
Figure 99
DuBois and coworkers, 2005
Figure 100
Figure 100
C(sp3)-C(sp3) Cross-Coupling Reaction (Kambe and coworkers, 2002)
Figure 101
Figure 101
Scope of Reaction (Kambe and coworkers, 2009)
Figure 102
Figure 102
Seminal Report (Kochi, 1971)
Figure 103
Figure 103
Scope (Cahiez and Coworkers, 1998)
Figure 104
Figure 104
Scope of Iron-Catalyzed Cross-Coupling (Fürstner and coworkers, 2002)
Figure 105
Figure 105
Cross-Coupling Reaction with Vinyl Triflates (Fürstner and coworkers, 2004)
Figure 106
Figure 106
Cross-Coupling of Alkenyl Carboxylates with Grignard Reagents (Shi and coworkers, 2009)
Figure 107
Figure 107
Iron-catalyzed C(sp3)-C(sp3) Coupling Reaction (Chai and coworkers, 2007)
Figure 108
Figure 108
Proposed Mechanisms
Figure 109
Figure 109
Polymer Supported Iron Catalyst for Ketone Formation (Taurino and coworkers)
Figure 110
Figure 110
Cross-Coupling of Acid Chlorides with Grignard Reagents (Fürstner and coworkers, 2004)
Figure 111
Figure 111
Selective Monoalkylation of Dichlorobenzene (Katayama and coworkers, 1991)
Figure 112
Figure 112
Cross-coupling Reaction with Enol Phosphonates (Miller, 2002)
Figure 113
Figure 113
Cross-Coupling Reaction of Vinyl and Aryl Tosylates (Hartwig and coworkers, 2005)
Figure 114
Figure 114
Synthesis of 2-(1H)-Pyrazinones (Eycken and coworkers, 2009)
Figure 115
Figure 115
Pd-Catalyzed C(sp3)-C(sp3) Coupling (Kambe and coworkers, 2003)
Figure 116
Figure 116
Preparation of Indium Reagents
Figure 117
Figure 117
Cross-Coupling with Aryl Halides (Sarandeses and coworkers, 2001)
Figure 118
Figure 118
Cross-Coupling with Alkenyl Triflates (Sarandeses and coworkers, 2001)
Figure 119
Figure 119
Stereoselective Cross-Coupling with Iodoalkenes (Sarandeses and coworkers, 2008)
Figure 120
Figure 120
Cross-Coupling with 1,1-Dibromoalkenes (Sarandeses and coworkers, 2008)
Figure 121
Figure 121
Cross-Coupling with Maleimides (Sarandeses and coworkers, 2009)
Figure 122
Figure 122
Carbonylative Cross-Couplings (Lee and coworkers, 2004)
Figure 123
Figure 123
Carbonylative Cross-Couplings (Lee and coworkers, 2004)
Figure 124
Figure 124
Oxidative Carbonylative Cross-Couplings (Lei and coworkers, 2008)
Figure 125
Figure 125
Cross-Coupling with Thioesters (Liebeskind and coworkers, 2005)
Figure 126
Figure 126
Methylation Reaction of Aryl Halides (Hiyama and coworkers, 1988)
Figure 127
Figure 127
Cross-Coupling of Aryl Triflate with Alkylsilicon (Hiyama and coworkers, 1990)
Figure 128
Figure 128
Cross-Coupling of Aryl halides with Alkylsilicon (Hiyama and coworkers, 1997)
Figure 129
Figure 129
2-(2-Hydroxyprop-2-yl)phenyl-Substituted Alkylsilanes in Cross-Coupling Reaction.
Figure 130
Figure 130
2-Alkylation of 2,3-Dichloro-1,4-naphthoquinone (Tam and coworkers, 1983)
Figure 131
Figure 131
2-Alkylation of Pyrazines (Ohta and coworkers, 1989)
Figure 132
Figure 132
Stille Coupling of Activated Alkyltin Reagents (Fouquet and coworkers, 2005)
Figure 133
Figure 133
Hiyama Coupling of Chiral Alkyl Silanes (Hiyama and coworkers, 1990)
Figure 134
Figure 134
Suzuki Coupling with Retention of Configuration (Crudden and coworkers, 2009)
Figure 135
Figure 135
Suzuki Coupling with Inversion of Configuration (Suginome and coworkers, 2010)
Figure 136
Figure 136
Negishi Coupling with Chiral Alkylzinc Reagent (Campos and coworkers, 2006)
Figure 137
Figure 137
Asymmetric Kumada Coupling (Aoyama and coworkers, 2004)
Figure 138
Figure 138
Asymmetric Negishi coupling with Benzylic Halides (Fu and coworkers, 2005)
Figure 139
Figure 139
Asymmetric Negishi Coupling with Allylic Chlorides (Fu and coworkers, 2008)
Figure 140
Figure 140
Asymmetric Suzuki Coupling with Homobenzylic Bromides (Fu and coworkers, 2008)
Figure 141
Figure 141
Total Synthesis using Alkylboron Reagents (2002–2004).
Figure 142
Figure 142
Total Synthesis using Alkylboron Reagents (2006–2009).
Figure 143
Figure 143
Total Synthesis Using Alkylboron Reagents (2009)
Figure 144
Figure 144
Application of B-alkyl Suzuki-Miyaura Cross-Coupling
Figure 145
Figure 145
Total Synthesis using Alkylzinc Reagents (2002–2003).
Figure 146
Figure 146
Total Synthesis using Alkylzinc Reagents (2004–2009).
Figure 147
Figure 147
Total Synthesis using Alkylzinc Reagents (2009–2010).
Figure 148
Figure 148
Application of Negishi Cross-Coupling,,
Figure 149
Figure 149
Total Synthesis using AlkylMg Reagents (2003–2010).
Scheme 1
Scheme 1
Cross-Couplings with Alkylzinc Reagents
Scheme 2
Scheme 2
PdCl2(dppf)-Catalyzed Negishi Coupling (Hayashi and coworkers, 1984)
Scheme 3
Scheme 3
Negishi Coupling with Homoallylic and Homopropargylic Alkylzinc Reagents (Negishi and coworkers, 1980)
Scheme 4
Scheme 4
Synthesis of Azamacrocycles via Negishi Coupling (Skerlj and coworkers, 2002)
Scheme 5
Scheme 5
Chemoselective Negishi Coupling of 2-bromo-pyridinylstannanes (Twieg and coworkers, 2008)
Scheme 6
Scheme 6
Pincer thioimido-Pd complex-Catalyzed Negishi Couplings (Lei and coworkers, 2008)
Scheme 7
Scheme 7
Aminoalkylation of Heteroarenes (Knochel and coworkers, 2007)
Scheme 8
Scheme 8
Hypothesis for Substrate-Controlled Negishi Coupling (Knochel and coworkers, 1999)
Scheme 9
Scheme 9
Secondary-Secondary Negishi Coupling in a Formal Total Synthesis of α-cembra-2,7,11-triene-4,6-diol (Fu and coworkers, 2008)
Scheme 10
Scheme 10
Stereochemistry in Tandem Cyclization-Cross-Couplings (Cárdenas and coworkers, 2007)
Scheme 11
Scheme 11
Identification of Mono Methyl Nickel-Complex (Vicic and coworkers, 2005)
Scheme 12
Scheme 12
Radical Mechanism in Ni-Catalyzed Alkyl-Alkyl Cross-Couplings (Vicic and coworkers, 2006)
Scheme 13
Scheme 13
Proposed Mechanism for Tandem Radical Cyclization Cross-Coupling (Cárdenas and coworkers, 2007)
Scheme 14
Scheme 14
Suzuki-Miyaura Catalytic Cycle
Scheme 15
Scheme 15
Role of Bases in Suzuki-Miyaura Coupling (Soderquist and coworkers, 1998)
Scheme 16
Scheme 16
Modified Suzuki-Miyaura Catalytic Cycle (Soderquist and coworkers, 1998)
Scheme 17
Scheme 17
Stereochemistry of the Pd-Catalyzed Oxidative Addition of Alkyl Tosylates (Fu and coworkers, 2002)
Scheme 18
Scheme 18
Mechanism of Transmetalation (Soderquist and coworkers, 1998)
Scheme 19
Scheme 19
Stereochemistry in Suzuki-Miyaura Couplings (Woerpel and coworkers, 1998)
Scheme 20
Scheme 20
Suzuki-Miyaura Coupling with a Steroidal Moiety (Suzuki and coworkers, 1989)
Scheme 21
Scheme 21
Suzuki-Miyaura Coupling with Electron-rich and Sterically Hindered Aryl Bromides (Buchwald and coworkers, 2004)
Scheme 22
Scheme 22
Alkylation of 2-halopurines (Piersanti and coworkers, 2010)
Scheme 23
Scheme 23
Suzuki Coupling in Quinoacridine-derivative Synthesis (Stevens and coworkers, 2003)
Scheme 24
Scheme 24
Intramolecular Suzuki-Miyaura Couplings
Scheme 25
Scheme 25
Carbonylative Suzuki Coupling of 2-iodo-glycal (Tan and coworkers, 2004)
Scheme 26
Scheme 26
Suzuki Coupling with Chlorobenzylidenelactone (Ma and coworkers, 2006)
Scheme 27
Scheme 27
Suzuki Coupling of Hindered Aryl Bromides (Delaude and coworkers, 2007)
Scheme 28
Scheme 28
Suzuki Coupling with Cyclopentylboronic Acid (Fu and coworkers, 2000)
Scheme 29
Scheme 29
Suzuki Coupling with Mixed Alkylboronic Esters (Falck and coworkers, 2001)
Scheme 30
Scheme 30
Comparative Study with Boron Derivatives (Molander and coworkers, 2001)
Scheme 31
Scheme 31
Selective Alkylation of Dichlorobenzene (Tam and coworkers, 1983)
Scheme 32
Scheme 32
Phenol-Directed Alkylation of Halobenzenes (Manabe and coworkers, 2009)
Scheme 33
Scheme 33
Tridentate Amido Diphosphino Ligand for Ni-Catalyzed Cross-Coupling (Liao and coworkers, 2006)
Scheme 34
Scheme 34
Synthesis of Alkylated Trifluoromethylbenzenes (Saint-Jalmes and Roques, 2006)
Scheme 35
Scheme 35
Synthesis of Unsymmetrically Substituted Quinoxaline (Ila and coworkers, 2005)
Scheme 36
Scheme 36
Use of Neopentyl Arenesulfonates in Cross-Coupling (Park and coworkers, 2005)
Scheme 37
Scheme 37
Initial Report (Kumada and coworkers, 1981)
Scheme 38
Scheme 38
Proposed Mechanism (Kambe and coworkers, 2002)
Scheme 39
Scheme 39
C-F Bond Functionalization (Kambe and coworkers, 2003)
Scheme 40
Scheme 40
Ni-catalyzed Kumada-Corriu Coupling with a Unique Pincer Amido-bis-(amine) Ligand (Hu and coworkers, 2008)
Scheme 41
Scheme 41
Proposed Mechanism (Kochi, 1971)
Scheme 42
Scheme 42
Effect of NMP on Reaction Outcome (Cahiez and coworkers, 1998)
Scheme 43
Scheme 43
Proposed Mechanism (Fürstner and coworkers, 2002)
Scheme 44
Scheme 44
Control Experiments (Fürstner and coworkers, 2002)
Scheme 45
Scheme 45
Superiority of Fe-Catalyzed Reaction over Ni-Catalyzed Reaction (Fürstner and coworkers, 2002)
Scheme 46
Scheme 46
Synthesis of 6-Methylpurine Bases (Hocek and coworkers, 2003)
Scheme 47
Scheme 47
Cross-Coupling of Chloroenynes with Grignard Reagents (Alami and coworkers, 2004)
Scheme 48
Scheme 48
Cross-Coupling of Imidoyl Chlorides with Grignard Reagents (Olsson, 2006)
Scheme 49
Scheme 49
Cross-Coupling of Heteroaromatic Sulfonates with Alkyl Grignards (Skrydstrup and coworkers, 2009)
Scheme 50
Scheme 50
Control Experiments (Chai and coworkers, 2007)
Scheme 51
Scheme 51
Different Reactivity for MeMgBr and EtMgBr
Scheme 52
Scheme 52
Proposed Mechanism for Reaction of Grignard Reagents Containing β-hydrogen with FeX2
Scheme 53
Scheme 53
Proposed Mechanism for Iron-Catalyzed Cross-Coupling
Scheme 54
Scheme 54
Selectivity of Pd- over Ni-Catalyst
Scheme 55
Scheme 55
Catalytic Cycle for Triorganoindium Reagents
Scheme 56
Scheme 56
Ni-Catalyzed Cross-Coupling with Aryl Chlorides (Sarandeses and coworkers, 2001)
Scheme 57
Scheme 57
Sequential Cross-Coupling (Sarandeses and coworkers, 2002)
Scheme 58
Scheme 58
Cross-Coupling in Aqueous Media (Oshima and coworkers, 2001)
Scheme 59
Scheme 59
Oxidative Cross-Couplings (Lei and coworkers, 2009)
Scheme 60
Scheme 60
Cross-Coupling with Acid Chlorides (Sarandeses and coworkers, 2001)
Scheme 61
Scheme 61
Proposed Mechanism (Hiyama and coworkers, 1997)
Scheme 62
Scheme 62
Proposed Mechanism for Inversion of Configuration
Scheme 63
Scheme 63
Synthesis of Gluocokinase Activator (Campos and coworkers, 2008)
Scheme 64
Scheme 64
Asymmetric Kumada Coupling with Chiral Ferrocenylphosphine Ligand (Kumada and coworkers, 1982)
Scheme 65
Scheme 65
Coordination-Assisted Chiral Induction Model (Kumada and coworkers, 1982)
Scheme 66
Scheme 66
Asymmetric Kumada Coupling with Chiral Sulfide Ligand (Kellogg and coworkers, 1986)
Scheme 67
Scheme 67
Asymmetric Synthesis of Cyclopentane Derivatives (Shibasaki and coworkers, 1998)
Scheme 68
Scheme 68
Asymmetric Kumada Coupling with Quinphos Ligand (Lemaire and coworkers, 2001)
Scheme 69
Scheme 69
Formal Total Synthesis of Fluvirucinine A1 (Fu and coworkers, 2008)
Scheme 70
Scheme 70
Total Synthesis of Anguinomycin (Bonazzi and Coworkers, 2010)
Scheme 71
Scheme 71
Total Synthesis of Oleandolide (Panek and coworkers, 2002)
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. de Meijere A, Diederich F, editors. In Metal-Catalyzed Cross-Coupling Reactions, Second Completely Revised and Enlarged Edition. Vol. 2. Wiley-VCH Verlag GmbH & Co; KGaA: 2004.
    1. de Meijere A, Diederich F, editors. Metal-Catalyzed Cross-Coupling Reactions, Second, Completely Revised and Enlarged Edition. Vol. 1. Wiley-VC CH Verlag GmbH & Co; KGaA: 2004.
    1. Diederich F, Stang PJ, editors. Metal-catalyzed Cross-Coupling Reactions. Wiley-VCH; Weinhein, Germany: 1998.
    1. Knochel P, Leuser H, Gong LZ, Perrone S, Kneisel FF. Chem Organozinc Compd. 2006:287.
    1. Knochel P, Leuser H, Gong L-Z, Perrone S, Kneisel FF. Polyfunctional zinc organometallics for organic synthesis. 2005;1

Publication types