doi: 10.1002/anie.201205747.
Epub 2012 Oct 4.
Pd-PEPPSI-IPent(Cl): a highly effective catalyst for the selective cross-coupling of secondary organozinc reagents
Affiliations
- PMID: 23038603
- DOI: 10.1002/anie.201205747
Item in Clipboard
Pd-PEPPSI-IPent(Cl): a highly effective catalyst for the selective cross-coupling of secondary organozinc reagents
Angew Chem Int Ed Engl.
.
Abstract
No migration? No problem! A series of new N-heterocyclic carbene based Pd complexes has been created and evaluated in the Negishi cross-coupling of aryl and heteroaryl chlorides, bromides, and triflates with a variety of secondary alkylzinc reagents. The direct elimination product is nearly exclusively formed; in most examples there is no migratory insertion at all.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
One-pot Negishi cross-coupling reactions of in situ generated zinc reagents with aryl chlorides, bromides, and triflates.J Org Chem. 2008 Sep 19;73(18):7380-2. doi: 10.1021/jo801063c. Epub 2008 Aug 12. J Org Chem. 2008. PMID: 18693766
-
Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent.Chem Commun (Camb). 2011 May 14;47(18):5181-3. doi: 10.1039/c0cc04835f. Epub 2011 Feb 1. Chem Commun (Camb). 2011. PMID: 21286604
-
An efficient low-temperature Stille-Migita cross-coupling reaction for heteroaromatic compounds by Pd-PEPPSI-IPent.Chemistry. 2010 Apr 12;16(14):4279-83. doi: 10.1002/chem.200903337. Chemistry. 2010. PMID: 20209529
-
From α-arylation of olefins to acylation with aldehydes: a journey in regiocontrol of the Heck reaction.Acc Chem Res. 2011 Aug 16;44(8):614-26. doi: 10.1021/ar200053d. Epub 2011 May 25. Acc Chem Res. 2011. PMID: 21612205 Review.
-
Palladium-based catalytic systems for the synthesis of conjugated enynes by sonogashira reactions and related alkynylations.Angew Chem Int Ed Engl. 2007;46(6):834-71. doi: 10.1002/anie.200602761. Angew Chem Int Ed Engl. 2007. PMID: 17335070 Review.
Cited by
-
Well-defined nickel and palladium precatalysts for cross-coupling.Nat Rev Chem. 2017;1:0025. doi: 10.1038/s41570-017-0025. Epub 2017 Mar 1. Nat Rev Chem. 2017. PMID: 29034333 Free PMC article.
-
The key role of R-NHC coupling (R = C, H, heteroatom) and M-NHC bond cleavage in the evolution of M/NHC complexes and formation of catalytically active species.Chem Sci. 2020 Jun 19;11(27):6957-6977. doi: 10.1039/d0sc02629h. eCollection 2020 Jul 21. Chem Sci. 2020. PMID: 33133486 Free PMC article. Review.
-
Rapid and Modular Access to Vinyl Cyclopropanes Enabled by Air-stable Palladium(I) Dimer Catalysis.Angew Chem Int Ed Engl. 2023 Feb 6;62(7):e202211167. doi: 10.1002/anie.202211167. Epub 2023 Jan 11. Angew Chem Int Ed Engl. 2023. PMID: 36226918 Free PMC article.
-
Emerging Trends in Cross-Coupling: Twelve-Electron-Based L1Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications.Chem Rev. 2022 Dec 14;122(23):16983-17027. doi: 10.1021/acs.chemrev.2c00204. Epub 2022 Oct 3. Chem Rev. 2022. PMID: 36190916 Free PMC article. Review.
-
A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents.Beilstein J Org Chem. 2015 Sep 17;11:1656-66. doi: 10.3762/bjoc.11.182. eCollection 2015. Beilstein J Org Chem. 2015. PMID: 26664586 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
