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Non-transition Metal-Mediated Diverse Aryl-Heteroatom Bond Formation of Arylammonium Salts.

ABSTRACT: Aryl-heteroatom (C-X) bonds ubiquitously exist in organic, medicinal, and material chemistry, but a universal method to construct diverse C-X bonds is lacking. Here we report our discovery of a convenient and efficient approach to construct various C-X bonds using arylammonium salts as the substrate via an S_NAr process. This strategy features mild reaction condition, no request of transition metal catalyst, and easy formation of various C-X bonds (C-S, C-Si, C-Sn, C-Ge, C-Se, C-N). The method was successfully applied to a late-stage functionalization of an existing antibiotic drug, to a Clickable reaction of NBD-based ammonium salt as turn-on fluorescent probe to recognize L-cysteine and homocysteine, and to the synthesis of a DNA encoded library (DEL) bearing different C-X bonds.

SUBMITTER: Wang DY

PROVIDER: S-EPMC6525302 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Non-transition Metal-Mediated Diverse Aryl-Heteroatom Bond Formation of Arylammonium Salts.

Wang Dong-Yu DY Wen Xin X Xiong Chao-Dong CD Zhao Jian-Nan JN Ding Chun-Yong CY Meng Qian Q Zhou Hu H Wang Chao C Uchiyama Masanobu M Lu Xiao-Jie XJ Zhang Ao A

iScience 20190503

Aryl-heteroatom (C-X) bonds ubiquitously exist in organic, medicinal, and material chemistry, but a universal method to construct diverse C-X bonds is lacking. Here we report our discovery of a convenient and efficient approach to construct various C-X bonds using arylammonium salts as the substrate via an S<sub>N</sub>Ar process. This strategy features mild reaction condition, no request of transition metal catalyst, and easy formation of various C-X bonds (C-S, C-Si, C-Sn, C-Ge, C-Se, C-N). Th ...[more]

PMID: 31102996

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