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Brønsted Acid Catalyzed PhSe Transfer versus Radical Aryl Transfer: Linear Codimerization of Styrenes and Internal Olefins

Author:
Wu, Ping, Wang, Liandi, Wu, Kaikai, Yu, Zhengkun
Source:
Organic letters 2015 v.17 no.4 pp. 868-871
ISSN:
1523-7052
Subject:
Bronsted acids, alkenes, chemical reactions, chemical structure, regioselectivity
Abstract:
Brønsted acid p-TsOH·H₂O-catalyzed hydrovinylation of styrenes with internal olefins α-oxo ketene dithioacetals was efficiently achieved in the presence of N-phenylselenophthalimide (N-PSP), regioselectively affording Markovnikov phenylselenative hydrovinylation products through PhSe transfer of the phenylseleno ketene dithioacetal intermediates. Radical reduction of the resultant PhSe-alkyl-substituted ketene dithioacetals with AIBN/n-Bu₃SnH gave the corresponding anti-Markovnikov hydrovinylation products formally from the linear codimerization of styrenes and the internal olefins.
Agid:
5790245