doi: 10.1021/ja072992f.
Epub 2007 Jul 12.
New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings
Affiliations
- PMID: 17628066
- PMCID: PMC2614909
- DOI: 10.1021/ja072992f
Item in Clipboard
New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings
J Am Chem Soc.
.
No abstract available
Similar articles
-
A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.J Am Chem Soc. 2010 May 12;132(18):6304-5. doi: 10.1021/ja102262v. J Am Chem Soc. 2010. PMID: 20394367 Free PMC article.
-
Ligand steric contours to understand the effects of N-heterocyclic carbene ligands on the reversal of regioselectivity in Ni-catalyzed reductive couplings of alkynes and aldehydes.J Am Chem Soc. 2011 May 11;133(18):6956-9. doi: 10.1021/ja202007s. Epub 2011 Apr 20. J Am Chem Soc. 2011. PMID: 21506540 Free PMC article.
-
NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.J Am Chem Soc. 2017 Jul 12;139(27):9317-9324. doi: 10.1021/jacs.7b04583. Epub 2017 Jul 3. J Am Chem Soc. 2017. PMID: 28621131 Free PMC article.
-
Nucleophilic carbenes as organocatalysts.Ernst Schering Found Symp Proc. 2007;(2):159-81. Ernst Schering Found Symp Proc. 2007. PMID: 18642525 Review.
-
Organocatalysis by N-heterocyclic carbenes.Chem Rev. 2007 Dec;107(12):5606-55. doi: 10.1021/cr068372z. Epub 2007 Oct 23. Chem Rev. 2007. PMID: 17956132 Review. No abstract available.
Cited by
-
Ni-catalyzed arylation of alkynes with organoboronic acids and aldehydes to access stereodefined allylic alcohols.Chem Sci. 2023 Jan 20;14(8):2040-2045. doi: 10.1039/d2sc05894d. eCollection 2023 Feb 22. Chem Sci. 2023. PMID: 36845934 Free PMC article.
-
Enantioselective conjugate silyl additions to cyclic and acyclic unsaturated carbonyls catalyzed by Cu complexes of chiral N-heterocyclic carbenes.J Am Chem Soc. 2010 Mar 10;132(9):2898-900. doi: 10.1021/ja910989n. J Am Chem Soc. 2010. PMID: 20148561 Free PMC article.
-
A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.J Am Chem Soc. 2010 May 12;132(18):6304-5. doi: 10.1021/ja102262v. J Am Chem Soc. 2010. PMID: 20394367 Free PMC article.
-
Enantioselective electroreductive alkyne-aldehyde coupling.Nat Commun. 2025 Jul 1;16(1):5686. doi: 10.1038/s41467-025-60230-5. Nat Commun. 2025. PMID: 40592859 Free PMC article.
-
Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones.Science. 2016 Jul 8;353(6295):144-50. doi: 10.1126/science.aaf7720. Epub 2016 Jun 9. Science. 2016. PMID: 27284169 Free PMC article.
References
-
- For nickel-catalyzed aldehyde / alkyne reductive couplings or cyclizations. - PubMed
- Oblinger E, Montgomery J. J. Am. Chem. Soc. 1997;119:9065.
- Tang X-Q, Montgomery J. J. Am. Chem. Soc. 1999;121:6098.
- Tang X-Q, Montgomery J. J. Am. Chem. Soc. 2000;122:6950.
- Huang W-S, Chan J, Jamison TF. Org. Lett. 2000;2:4221. - PubMed
- Takai K, Sakamoto S, Isshiki T. Org. Lett. 2003;5:653. - PubMed
- Montgomery J. Angew. Chem. Int. Ed. 2004;43:3890. For a review, see. - PubMed
-
- For aldehyde / alkyne reductive couplings using other metals.
- Srebnik M. Tetrahedron Lett. 1991;32:2449.
- Kataoka Y, Miyai J, Oshima K, Takai K, Utimoto K. J. Org. Chem. 1992;57:1973.
- Wipf P, Xu W. Tetrahedron Lett. 1994;35:5197.
- Crowe WE, Rachita MJ. J. Am. Chem. Soc. 1995;117:6787.
- Chen YK, Walsh PJ. J. Am. Chem. Soc. 2004;126:3702. - PubMed
- Bahadoor AB, Flyer A, Micalizio GC. J. Am. Chem. Soc. 2005;127:3694. - PubMed
-
- Oppolzer W, Radinov RN. Helv. Chem. Acta. 1992;75:170.
- Oppolzer W, Radinov RN. J. Am. Chem. Soc. 1993;115:1593.
- Oppolzer W, Radinov RN, El-Sayed E. J. Org. Chem. 2001;66:4766. - PubMed
- Wipf P, Ribe S. J. Org. Chem. 1998;63:6454.
- Miller KM, Huang W-S, Jamison TF. J. Am. Chem. Soc. 2003;125:3442. - PubMed
- Colby EA, Jamison TF. J. Org. Chem. 2003;68:156. - PubMed
- Komanduri V, Krische MJ. J. Am. Chem. Soc. 2006;128:16448. - PubMed
- Kong J-R, Ngai M-Y, Krische MJ. J. Am. Chem. Soc. 2006;128:718. - PubMed
- Rhee JU, Krische MJ. J. Am. Chem. Soc. 2006;128:10674. - PubMed
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
