In:
Angewandte Chemie, Wiley, Vol. 133, No. 1 ( 2021-01-04), p. 384-388
Abstract:
The development of enantioconvergent cross‐coupling of racemic alkyl halides directly with heteroarene C(sp 2 )−H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona‐alkaloid‐derived N , N , P ‐ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp 2 )−H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α‐chiral alkylated azoles, such as 1,3,4‐oxadiazoles, oxazoles, and benzo[ d ]oxazoles as well as 1,3,4‐triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp 2 )−H bond and the involvement of alkyl radical species under the reaction conditions.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.202009527
Language:
English
Publisher:
Wiley
Publication Date:
2021
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1479266-7
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