Synthesis of α-Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates

The synthesis of sterically congested amides was accomplished via Cp*Co(III)-catalyzed sequential C-H bond addition to 1,3-dienes followed by aminocarbonylation with isocyanates, a coupling partner that had never been utilized in sequential C-H bond addition reactions. A variety of C-H bond reactants, internally substituted dienes, and aromatic isocyanates provided secondary amide products incorporating α-all-carbon quaternary centers. The conversion of the amide products to other useful compound classes was also demonstrated.

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Publication Details

Journal
Organic Letters
Published
2024-10-31
DOI
https://doi.org/10.1021/acs.orglett.4c03740
Citations
9
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.25

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article

Synthesis of α-Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates

Jonathan A. Ellman, Jihyeon Yeo, Joseph P. Tassone
9 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.25
article

Synthesis of α-Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates

Jonathan A. Ellman, Jihyeon Yeo, Joseph P. Tassone
article en
9 citations

Abstract

The synthesis of sterically congested amides was accomplished via Cp*Co(III)-catalyzed sequential C-H bond addition to 1,3-dienes followed by aminocarbonylation with isocyanates, a coupling partner that had never been utilized in sequential C-H bond addition reactions. A variety of C-H bond reactants, internally substituted dienes, and aromatic isocyanates provided secondary amide products incorporating α-all-carbon quaternary centers. The conversion of the amide products to other useful compound classes was also demonstrated.

Organic LettersVol. 26(45)
Yale University (US)
National Institutes of Health, National Institute of General Medical Sciences
Openalex Percentile: Top 12%
Catalytic C–H Functionalization Methods
2.25
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