Electronically Matching C-H Alkylation Strategies for the Synthesis of alpha-Heteroaryl Acetic Acid Derivatives
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초록

A strategy in which complementary species are paired for the preparation of alpha-heteroaryl esters and amides from heteroarenes was developed. Readily available alpha-haloacetates and alpha-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 alpha-heteroaryl acetic acid derivatives and expand the scope of heteroarenes that can be utilized for C-H alkylation.

키워드

C-H activationcross-couplingphotocatalysisvicarious nucleophilic aromatic substitutionalpha-heteroaryl acetic acid derivativesVICARIOUS NUCLEOPHILIC-SUBSTITUTIONCATALYZED DIRECT ALKYLATIONLIGHT PHOTOREDOX CATALYSISCROSS-COUPLING REACTIONARYLBORONIC ACIDSBORONIC ACIDSPENTATOMIC HETEROAROMATICSC(SP(2))-H BONDSC(SP(3))-H BONDSDIRECT ARYLATION
제목
Electronically Matching C-H Alkylation Strategies for the Synthesis of alpha-Heteroaryl Acetic Acid Derivatives
저자
Jang, Ha-LimKim, Hyun TaeCho, Eun JinJoo, Jung Min
DOI
10.1002/ajoc.201500388
발행일
2015-12
유형
Article
저널명
Asian Journal of Organic Chemistry
4
12
페이지
1386 ~ 1391