Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.
Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.
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有机化学。使用瞬态指导组对C（SP3）-H键的功能化。
DOI：
10.1126/science.aad7893
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发表时间：
2016-01-15
期刊：
影响因子：
--
通讯作者：
Yu JQ
中科院分区：
文献类型：
--
作者：
Zhang FL;Hong K;Li TJ;Park H;Yu JQ
Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in C–H bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and often applicability as well. Herein, we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C–H bonds. Arylation of a wide range of aldehydes and ketones at the β- or γ-positions proceeds in the presence of a Pd catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C–H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.
