Carbene Catalysts

Overview

Journal Top Curr Chem

Specialty Chemistry

Date 2011 Apr 16

PMID 21494949

Citations 44

Authors

Jennifer L Moore

Tomislav Rovis

Affiliations

Soon will be listed here.

Abstract

The use of N-heterocyclic carbenes as catalysts for organic transformations has received increased attention in the past 10 years. A discussion of catalyst development and nucleophilic characteristics precedes a description of recent advancements and new reactions using N-heterocyclic carbenes in catalysis.

Citing Articles

Mechanism and stereoselectivity in NHC-catalyzed β-functionalization of saturated carboxylic ester.

Li Y, Zhang Z RSC Adv. 2022; 9(14):7635-7644.

PMID: 35521168 PMC: 9061211. DOI: 10.1039/c8ra10262g.

MOF-Zn-NHC as an efficient N-heterocyclic carbene catalyst for aerobic oxidation of aldehydes to their corresponding carboxylic acids a cooperative geminal anomeric based oxidation.

Babaee S, Zarei M, Zolfigol M RSC Adv. 2022; 11(57):36230-36236.

PMID: 35492781 PMC: 9043340. DOI: 10.1039/d1ra05494e.

Photoredox-Catalyzed C-H Functionalization Reactions.

Holmberg-Douglas N, Nicewicz D Chem Rev. 2021; 122(2):1925-2016.

PMID: 34585909 PMC: 8939264. DOI: 10.1021/acs.chemrev.1c00311.

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

Davies A, Greenhalgh M, Slawin A, Smith A Beilstein J Org Chem. 2020; 16:1572-1578.

PMID: 32704323 PMC: 7356285. DOI: 10.3762/bjoc.16.129.

Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.

Zhao C, Guo D, Munkerup K, Huang K, Li F, Wang J Nat Commun. 2018; 9(1):611.

PMID: 29426851 PMC: 5807440. DOI: 10.1038/s41467-018-02952-3.

References

Reynolds N, Read de Alaniz J, Rovis T . Conversion of alpha-haloaldehydes into acylating agents by an internal redox reaction catalyzed by nucleophilic carbenes. J Am Chem Soc. 2004; 126(31):9518-9. DOI: 10.1021/ja046991o. View

Nicolaou K, Tang Y, Wang J . Formal synthesis of (+/-)-platensimycin. Chem Commun (Camb). 2007; (19):1922-3. DOI: 10.1039/b704589a. View

Enders D, Niemeier O, Balensiefer T . Asymmetric intramolecular crossed-benzoin reactions by N-heterocyclic carbene catalysis. Angew Chem Int Ed Engl. 2006; 45(9):1463-7. DOI: 10.1002/anie.200503885. View

Bausch C, Johnson J . Cross silyl benzoin additions catalyzed by lanthanum tricyanide. J Org Chem. 2004; 69(12):4283-5. DOI: 10.1021/jo0496143. View

Burstein C, Glorius F . Organocatalyzed conjugate umpolung of alpha,beta-unsaturated aldehydes for the synthesis of gamma-butyrolactones. Angew Chem Int Ed Engl. 2004; 43(45):6205-8. DOI: 10.1002/anie.200461572. View

Roth B, Blankley C, Chucholowski A, Ferguson E, Hoefle M, Ortwine D . Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran-2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus. J Med Chem. 1991; 34(1):357-66. DOI: 10.1021/jm00105a056. View

Frantz D, Morency L, Soheili A, Murry J, Grabowski E, Tillyer R . Synthesis of substituted imidazoles via organocatalysis. Org Lett. 2004; 6(5):843-6. DOI: 10.1021/ol0498803. View

Nemirowski A, R Schreiner P . Electronic stabilization of ground state triplet carbenes. J Org Chem. 2007; 72(25):9533-40. DOI: 10.1021/jo701615x. View

Chow K, Bode J . Catalytic generation of activated carboxylates: direct, stereoselective synthesis of beta-hydroxyesters from epoxyaldehydes. J Am Chem Soc. 2004; 126(26):8126-7. DOI: 10.1021/ja047407e. View

10.

Harrington P, Tius M . Synthesis and absolute stereochemistry of roseophilin. J Am Chem Soc. 2001; 123(35):8509-14. DOI: 10.1021/ja011242h. View

11.

Harrington P, Tius M . A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core. Org Lett. 2000; 1(4):649-51. DOI: 10.1021/ol990124k. View

12.

He J, Zheng J, Liu J, She X, Pan X . N-heterocyclic carbene catalyzed nucleophilic substitution reaction for construction of benzopyrones and benzofuranones. Org Lett. 2006; 8(20):4637-40. DOI: 10.1021/ol061924f. View

13.

Tachibana Y, Kihara N, Takata T . Asymmetric benzoin condensation catalyzed by chiral rotaxanes tethering a thiazolium salt moiety via the cooperation of the component: can rotaxane be an effective reaction field?. J Am Chem Soc. 2004; 126(11):3438-9. DOI: 10.1021/ja039461l. View

14.

Sentman A, Csihony S, Waymouth R, Hedrick J . Silver(I)-carbene complexes/ionic liquids: novel N-heterocyclic carbene delivery agents for organocatalytic transformations. J Org Chem. 2005; 70(6):2391-3. DOI: 10.1021/jo048555q. View

15.

Bharadwaj A, Scheidt K . Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-Stetter/Paal-Knorr strategy. Org Lett. 2004; 6(14):2465-8. DOI: 10.1021/ol049044t. View

16.

Sohn S, Rosen E, Bode J . N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes. J Am Chem Soc. 2004; 126(44):14370-1. DOI: 10.1021/ja044714b. View

17.

Fukuda Y, Maeda Y, Kondo K, Aoyama T . Cyano-phosphorylation of aldehydes catalyzed by a nucleophilic N-heterocyclic carbene. Chem Pharm Bull (Tokyo). 2006; 54(3):397-8. DOI: 10.1248/cpb.54.397. View

18.

Maki B, Chan A, Phillips E, Scheidt K . Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes. Org Lett. 2007; 9(2):371-4. DOI: 10.1021/ol062940f. View

19.

Linghu X, Potnick J, Johnson J . Metallophosphites as umpolung catalysts: the enantioselective cross silyl benzoin reaction. J Am Chem Soc. 2004; 126(10):3070-1. DOI: 10.1021/ja0496468. View

20.

Chan A, Scheidt K . Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes. J Am Chem Soc. 2007; 129(17):5334-5. PMC: 2582183. DOI: 10.1021/ja0709167. View