Coordination Assisted Distal C-H Alkylation of Fused Heterocycles

Autor:	Sadhan Jana, Debabrata Maiti, Kankanala Ramakrishna, Jyoti Prasad Biswas, Tapas Kumar Achar, Sandip Porey
Rok vydání:	2019
Předmět:	Nitrile 010405 organic chemistry Quinoline General Medicine General Chemistry Benzoxazole Alkylation 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Benzothiazole Covalent bond Bifunctional Thiazole
Zdroj:	Angewandte Chemie (International ed. in English). 58(39)
ISSN:	1521-3773
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7a21c3339f0a127bfe4f3daec90e4938 https://pubmed.ncbi.nlm.nih.gov/31336005 Zobrazit plný text záznamu Plný text