Premium
Rh‐Catalyzed Carboxylates Directed C–H Activation for the Synthesis of ortho ‐Carboxylic 2‐Arylethenesulfonyl Fluorides: Access to Unique Electrophiles for SuFEx Click Chemistry
Author(s) -
Wang ShiMeng,
Moku Balakrishna,
Leng Jing,
Qin HuaLi
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800762
Subject(s) - chemistry , electrophile , catalysis , fluoride , carboxylic acid , combinatorial chemistry , covalent bond , click chemistry , organic chemistry , medicinal chemistry , inorganic chemistry
The first Rh III ‐catalyzed activation of ortho ‐C–H bonds of arylcarboxylic esters for monoselective coupling with ethenesulfonyl fluoride (ESF) was developed. This protocol provides a convenient access to a class of otherwise difficult to access 2‐arylethenesulfonyl fluorides possessing ortho ‐carboxylic esters functionality. The synthesized 25 examples in up to 99 % isolated yields of 2‐arylethenesulfonyl fluorides bearing versatile carboxylic groups make this method remarkably applicable in developing biologically and pharmacologically active ethenesulfonyl fluorides, which are potential covalent drug candidates.