In:
Angewandte Chemie, Wiley, Vol. 131, No. 32 ( 2019-08-05), p. 11229-11234
Abstract:
The first copper(I)‐catalyzed enantioselective borylation of racemic benzyl chlorides has been realized by a quadrant‐by‐quadrant structure modulation of QuinoxP*‐type bisphosphine ligands. This reaction converts racemic mixtures of secondary benzyl chlorides into the corresponding chiral benzylboronates with high enantioselectivity (up to 92 % ee ). The results of mechanistic studies suggest the formation of a benzylic radical intermediate. The results of DFT calculations indicate that the optimal bisphosphine‐copper(I) catalyst engages in noncovalent interactions that efficiently recognize the radical intermediate, and leads to high levels of enantioselectivity.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v131.32
DOI:
10.1002/ange.201906011
Language:
English
Publisher:
Wiley
Publication Date:
2019
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