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

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

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...

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Veröffentlicht in:Organic letters 2015-02, Vol.17 (4), p.868-871
Hauptverfasser: Wu, Ping, Wang, Liandi, Wu, Kaikai, Yu, Zhengkun
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container_title Organic letters
container_volume 17
creator Wu, Ping
Wang, Liandi
Wu, Kaikai
Yu, Zhengkun
description 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.
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title Brønsted Acid Catalyzed PhSe Transfer versus Radical Aryl Transfer: Linear Codimerization of Styrenes and Internal Olefins
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