Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 11, Pages 4558-4563Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b01124
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Funding
- NSFC [21572201, 21772170]
- National Basic Research Program of China [2015CB856600]
- Fundamental Research Funds for the Central Universities [2018XZZX001-02]
- Zhejiang Provincial NSFC [LR17B020001]
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The first Pd(II)-catalyzed enantioselective alkynylation of unbiased methylene beta-C(sp(3))-H bonds is reported. The readily accessible and tunable BINOL derivatives are used as chiral ligands in C-H activation for the first time. 3,3'-Fluorinated-BINOL proved crucial in determining both the reactivity and enantioselectivity. A wide range of carboxylic acid derivatives are well tolerated with high enantioselectivities (up to 96% ee). Mechanistic studies suggest that multiple ligands may participate in the stereodetermining C-H palladation step, and a chiral amplification effect is observed.
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