Asymmetric Constructionof a SeCF<sub>3</sub>‑SubstitutedStereocenterby CuH-Catalyzed Hydroboration of 1‑SeCF<sub>3</sub>‑Alkenes

A copper hydride (CuH)-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylseleno (SeCF<sub>3</sub>)-alkenes with H–Bpin has been developed. The regio- and enantioselective hydrocupration of an <i>in situ</i> generated CuH species is followed by a boration reaction to successfully construct a SeCF<sub>3</sub>- and Bpin-substituted chiral carbon center. The key to success is the appropriate choice of <i>t</i>Bu-modified biphosphine ligands, which enables an overwhelming high reaction efficiency.

Publication Details

Journal
Figshare
Published
2025-02-20
DOI
https://doi.org/10.1021/acs.orglett.5c00330.s001
Primary Topic
Cocoa and Sweet Potato Agronomy
Type
article
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article

Asymmetric Constructionof a SeCF3‑SubstitutedStereocenterby CuH-Catalyzed Hydroboration of 1‑SeCF3‑Alkenes

Figshare
Cocoa and Sweet Potato Agronomy
article

Asymmetric Constructionof a SeCF3‑SubstitutedStereocenterby CuH-Catalyzed Hydroboration of 1‑SeCF3‑Alkenes

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Abstract

A copper hydride (CuH)-catalyzed regio- and enantioselective hydroboration of 1-trifluoromethylseleno (SeCF<sub>3</sub>)-alkenes with H–Bpin has been developed. The regio- and enantioselective hydrocupration of an <i>in situ</i> generated CuH species is followed by a boration reaction to successfully construct a SeCF<sub>3</sub>- and Bpin-substituted chiral carbon center. The key to success is the appropriate choice of <i>t</i>Bu-modified biphosphine ligands, which enables an overwhelming high reaction efficiency.

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Cocoa and Sweet Potato Agronomy
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Asymmetric Constructionof a SeCF<sub>3</sub>‑SubstitutedStereocenterby CuH-Catalyzed Hydroboration of 1‑SeCF<sub>3</sub>‑Alkenes · Figshare (2025) | TGRS Research Map | TGRS