Electronically Matching C-H Alkylation Strategies for the Synthesis of alpha-Heteroaryl Acetic Acid Derivatives
- Authors
- Jang, Ha-Lim; Kim, Hyun Tae; Cho, Eun Jin; Joo, Jung Min
- Issue Date
- Dec-2015
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- C-H activation; cross-coupling; photocatalysis; vicarious nucleophilic aromatic substitution; alpha-heteroaryl acetic acid derivatives
- Citation
- ASIAN JOURNAL OF ORGANIC CHEMISTRY, v.4, no.12, pp 1386 - 1391
- Pages
- 6
- Journal Title
- ASIAN JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 4
- Number
- 12
- Start Page
- 1386
- End Page
- 1391
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/8883
- DOI
- 10.1002/ajoc.201500388
- ISSN
- 2193-5807
2193-5815
- Abstract
- 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.
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Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
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