期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 46, 页码 19652-19659出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09125
关键词
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资金
- National Natural Science Foundation of China [21722203, 21831002, 21801116]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Guangdong Innovative Program [2019BT02Y335]
- Natural Science Foundation of Guangdong Province [2018A030310083]
- Shenzhen Special Funds [JCYJ20180302180235837]
- SUSTech Special Fund for the Construction of High-Level Universities [G02216303]
A copper-catalyzed enantioconvergent Suzuki-Miyaura C(sp(3))-C(sp(2)) cross-coupling of various racemic alkyl halides with organoboronate esters has been established in high enantioselectivity. Critical to the success is the use of a chiral cinchona alkaloid-derived N,N,P-ligand for not only enhancing the reducing capability of copper catalyst to favor a stereoablative radical pathway over a stereospecific S(N)2-type process but also providing an ideal chiral environment to achieve the challenging enantiocontrol over the highly reactive radical species. The reaction has a broad scope with respect to both coupling partners, covering aryl- and heteroarylboronate esters, as well as benzyl-, heterobenzyl-, and propargyl bromides and chlorides with good functional group compatibility. Thus, it provides expedient access toward a range of useful enantioenriched skeletons featuring chiral tertiary benzylic stereocenters.
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