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  • Title: Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2 )-H Bonds.
    Author: Su XL, Ye L, Chen JJ, Liu XD, Jiang SP, Wang FL, Liu L, Yang CJ, Chang XY, Li ZL, Gu QS, Liu XY.
    Journal: Angew Chem Int Ed Engl; 2021 Jan 04; 60(1):380-384. PubMed ID: 32949177.
    Abstract:
    The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2 )-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(sp2 )-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(sp2 )-H bond and the involvement of alkyl radical species under the reaction conditions.
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