期刊
ISCIENCE
卷 21, 期 -, 页码 490-+出版社
CELL PRESS
DOI: 10.1016/j.isci.2019.10.048
关键词
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资金
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Science Foundation of China [21971228, 21772187]
The direct functionalization of C(sp(3))-H bonds has led to the development of methods to access molecules or intermediates from basic chemicals in an atom- and step-economic fashion. Nevertheless, achieving high levels of chemo-, region and enantioselectivity in these reactions remains challenging due to the ubiquity and low reactivity of C(sp(3))-H bonds. Herein, we report an unprecedented protocol for enantioselective cyanation of remote C(sp(3))-H bonds. With chiral Box-Cu complex as the catalyst, the reaction of N-fluorosulfonamide furnishes the corresponding products in excellent yields and high enantiomeric excess (ee) under mild reaction conditions. A radical relay pathway involving 1,5-hydrogen atom transfer (1,5-HAT) of N-center radicals followed by enantioselective cyanation of the in situ-formed benzyl radicals is proposed. This enantioselective copper-catalyzed cyanation thus offers insights into an efficient way for the synthesis of bioactive molecules for drug discovery.
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