Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide | Zendy

ShyhMing Yang | Zendy; Sandip K. Nandy | Zendy; Anandakathir Robinson Selvakumar | Zendy; JimMin Fang | Zendy

Open Access

Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide

Author(s) -

ShyhMing Yang,

Sandip K. Nandy,

Anandakathir Robinson Selvakumar,

JimMin Fang

Publication year - 2000

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol006628w

Subject(s) - chemistry , thiophene , carboxylate , raney nickel , surface modification , electrophile , organic chemistry , medicinal chemistry , samarium , conjugated system , polymer chemistry , catalysis , polymer

Methyl thiophene-2-carboxylate, methyl 3-(thien-2-yl)acrylate, and methyl 5,2'-bithiophene-2-carboxylate were utilized as the synthetic equivalents of pentanoate 5-anion, pentanoate 4,5-dianion, heptanoate 7-anion, and nonanoate-8,9-dianion. By the promotion of samarium diiodide, these thiophene-incorporating compounds reacted with aldehydes, ketones, and conjugated esters regioselectively at the thienyl rings. Long-chain esters with remote hydroxyl and carboxyl groups, including an antiarthritis agent, a shellac component, and an inhibitory agent of spore germination, were prepared after reductive desulfurization on Raney nickel.

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