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Rhodium‐Catalyzed Additive‐Free C−H Ethoxycarbonylation of (Hetero)Arenes with Diethyl Dicarbonate as a CO Surrogate
Author(s) -
Suzuki Hirotsugu,
Liao Yumeng,
Kawai Yuya,
Matsuda Takanori
Publication year - 2021
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.202100956
Subject(s) - chemistry , rhodium , catalysis , amide , ethanol , indole test , organic chemistry , medicinal chemistry , combinatorial chemistry
A rhodium‐catalyzed C(sp 2 )‐H ethoxycarbonylation of indoles and arylpyridines using diethyl dicarbonate was developed. The catalytic process features an additive‐free ethoxycarbonylation reaction, in which only ethanol and CO 2 are produced as byproducts, providing a CO‐free and operationally simple protocol. The introduced ethoxycarbonyl group is easily transformed into other ester and amide functionalities in a single step. Moreover, the reaction can be successfully applied on gram scale, and allows for the efficient synthesis of indole‐2‐carboxylic acid esters and isophthalates.