Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 39, Pages 13808-13812Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907544
Keywords
alkylation; bifunctional; C-H activation; heterocycles; non-covalent
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Funding
- SERB, India [CRG/2018/003951]
- IIT Bombay
- CSIR-India
- SERB-NPDF [PDF/2016/002187]
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Distal C-H bond functionalization of heterocycles remained extremely challenging with covalently attached directing groups (DG). Lack of proper site for DG attachment and inherent catalyst poisoning by heterocycles demand alternate routes for site selective functionalization of their distal C-H bonds. Utilizing non-productive coordinating property to hold the heterocycle into the cavity of a template system in a host-guest manner, we report distal C-H alkylation (C-5 of quinoline and thiazole, C-7 of benzothiazole and benzoxazole) of heterocycles. Upon complexation with heterocyclic substrate, nitrile DG in template directs the metal catalyst towards close vicinity of the specific distal C-H bond of the heterocycles. Our hypothesized pathway has been supported by various X-ray crystallographically characterized intermediates.
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