Brønsted acid-catalyzed phenylselenenylation of internal olefins. Issue 19 (6th May 2015)

• Record Type: Journal Article
• Authors: Wu, Ping; Huang, Fei; Lou, Jiang; Wang, Quannan; Liu, Zhuqing; Yu, Zhengkun
• Is Part Of: Tetrahedron letters. Volume 56:Issue 19(2015)
• Page Start: 2488
• Page End: 2491
• Publication Date: 2015-05-06
• Subjects: Brønsted acid -- Internal olefins -- Phenylselenenylation -- N-phenylselenophthalimide -- Phenylseleno transfer; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.03.096
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Brønsted acid p -TsOH·H2 O-catalyzed phenylselenenylation of α-oxo ketene dithioacetals was efficiently achieved by using N -phenylselenophthalimide ( N -PSP) as the phenylseleno reagent. The resultant selenated ketene dithioacetals reacted with styrene in the presence of the same acid to undergo PhSe group transfer, regioselectively affording Markovnikov-type PhSe-alkylated olefins. Their further transformation with phenylboronic acid, guanidine, and hydrazine offers a promising route to access S, Se-incorporated organic compounds.