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Electronically Matching C−H Alkylation Strategies for the Synthesis of α‐Heteroaryl Acetic Acid Derivatives
Author(s) -
Jang HaLim,
Kim Hyun Tae,
Cho Eun Jin,
Joo Jung Min
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500388
Subject(s) - chemistry , alkylation , electrophile , acetic acid , carbanion , acetamide , nucleophile , combinatorial chemistry , organic chemistry , radical , primary (astronomy) , catalysis , physics , astronomy
A strategy in which complementary species are paired for the preparation of α‐heteroaryl esters and amides from heteroarenes was developed. Readily available α‐haloacetates and α‐acetamides provided the requisite acetate and acetamide groups via three distinctive reactive species, namely nucleophilic carbanions, alkylpalladium complexes, and photoredox‐generated electrophilic radicals. Based on their electronic properties, these intermediates were matched with various five‐membered heteroarenes, such as pyrazoles, imidazoles, thiophenes, furans, pyrroles, and indoles. These flexible protocols offer easy access to α‐heteroaryl acetic acid derivatives and expand the scope of heteroarenes that can be utilized for C−H alkylation.