Asymmetric CuI-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si–H Bonds | Zendy

Virginie Carreras | Zendy; C. Besnard | Zendy; Vincent Gandon | Zendy; Thierry Ollevier | Zendy

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Asymmetric Cu^I-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si–H Bonds

Author(s) -

Virginie Carreras,

C. Besnard,

Vincent Gandon,

Thierry Ollevier

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03480

Subject(s) - silanes , chemistry , diimine , aryl , catalysis , copper , insertion reaction , solvent , medicinal chemistry , stereochemistry , organic chemistry , silane , alkyl

An asymmetric copper(I)-catalyzed Si-H insertion reaction of 1-aryl-2,2,2-trifluoro-1-diazoethanes in dimethyl carbonate as a green solvent alternative was developed. A C 2 -symmetric copper(I) diimine complex enabled the asymmetric insertion reaction to give enantioenriched (1-aryl-2,2,2-trifluoroethyl)silanes with excellent stereoselectivities (up to 98:2 er ). Successful conversion of the silanes into the corresponding alcohols was performed with retention of stereochemistry. Mechanistic studies and DFT calculations support the proposed model for the observed stereoselectivities.

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