Noncovalent N-Heterocyclic Carbene Catalysis Enables Asymmetric Conjugate Addition of 2-Benzofuranones to Terminal C-Electrophiles

Herein, we report asymmetric conjugate addition of 2-benzofuranones to fully unsubstituted carbon electrophiles using noncovalent N-heterocyclic carbene (NHC) catalysis. Employing a confined chiral bifunctional NHC having a free -OH group as catalyst, the method furnishes various functionalized 2-benzofuranones bearing an all-carbon quaternary stereogenic center with broad scope, high yields, and excellent er's. Control studies suggest the concurrent activation of both partners by the bifunctional NHC.

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Journal
Organic Letters
Published
2025-11-06
DOI
https://doi.org/10.1021/acs.orglett.5c03865
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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article

Noncovalent N-Heterocyclic Carbene Catalysis Enables Asymmetric Conjugate Addition of 2-Benzofuranones to Terminal C-Electrophiles

Pradip Bhunia, Bhaskar Mondal, Joyram Guin, Sadhan Gorai
Organic Letters
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

Noncovalent N-Heterocyclic Carbene Catalysis Enables Asymmetric Conjugate Addition of 2-Benzofuranones to Terminal C-Electrophiles

Pradip Bhunia, Bhaskar Mondal, Joyram Guin, Sadhan Gorai
article en

Abstract

Herein, we report asymmetric conjugate addition of 2-benzofuranones to fully unsubstituted carbon electrophiles using noncovalent N-heterocyclic carbene (NHC) catalysis. Employing a confined chiral bifunctional NHC having a free -OH group as catalyst, the method furnishes various functionalized 2-benzofuranones bearing an all-carbon quaternary stereogenic center with broad scope, high yields, and excellent er's. Control studies suggest the concurrent activation of both partners by the bifunctional NHC.

Organic LettersVol. 27(46)
Indian Association for the Cultivation of Science (IN)
Openalex Percentile: Top 75%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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