期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 24, 页码 10571-10591出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04074
关键词
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资金
- Scripps Research Institute
- NIH (National Institute of General Medical Sciences) [R01 GM102265]
- NSF under the CCI Center for Selective CH Functionalization [CHE-1205646]
- Lindemann Trust
The ability to differentiate between highly similar C-H bonds in a given molecule remains a fundamental challenge in organic chemistry. In particular, the lack of sufficient steric and electronic differences between C-H bonds located distal to functional groups has prevented the development of site-selective catalysts with broad scope. An emerging approach to circumvent this obstacle is to utilize the distance between a target C-H bond and a coordinating functional group, along with the geometry of the cyclic transition state in directed C-H activation, as core molecular recognition parameters to differentiate between multiple C-H bonds. In this Perspective, we discuss the advent and recent advances of this concept. We cover a wide range of transition-metal-catalyzed, template-directed remote C-H activation reactions of alcohols, carboxylic acids, sulfonates, phosphonates, and amines. Additionally, we review eminent examples which take advantage of non-covalent interactions to achieve regiocontrol. Continued advancement of this distance- and geometry-based differentiation approach for regioselective remote C-H functionalization reactions may lead to the ultimate realization of molecular editing: the freedom to modify organic molecules at any site, in any order.
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