A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide1

Autor:	H. P. Dijkstra, Ronald ten Have, A. M. Van Leusen
Rok vydání:	1998
Předmět:	Steric effects chemistry.chemical_compound Chemistry Bromobenzene Aryl Organic Chemistry TosMIC Organic chemistry Tosylmethyl isocyanide Medicinal chemistry Derivative (chemistry) Coupling reaction Stille reaction
Zdroj:	The Journal of Organic Chemistry. 63:5332-5338
ISSN:	1520-6904 0022-3263
Popis:	A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael acceptors. Stille cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo-coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4e55ca1bf266849871cd708a2d418497 https://doi.org/10.1021/jo972216y Zobrazit plný text záznamu