Synthesis 2016; 48(04): 520-534
DOI: 10.1055/s-0035-1560380
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Allylation of Carbon Electrophiles with Alkenyl­silanes under Dual Catalysis by Cationic Platinum(II) Species

Hidenori Kinoshita
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan   Email: kmiura@apc.saitama-u.ac.jp
,
Ryosuke Kizu
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan   Email: kmiura@apc.saitama-u.ac.jp
,
Masahiro Horikoshi
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan   Email: kmiura@apc.saitama-u.ac.jp
,
Gen Inoue
b  Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
,
Masayuki Fujimoto
b  Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
,
Masanori Saito
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan   Email: kmiura@apc.saitama-u.ac.jp
,
Junji Ichikawa
b  Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
,
Akira Hosomi
b  Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
,
Katsukiyo Miura*
a  Department of Applied Chemistry, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan   Email: kmiura@apc.saitama-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 12 October 2015

Accepted after revision: 05 November 2015

Publication Date:
16 December 2015 (online)


Abstract

In the presence of catalytic amounts of platinum(II) chloride and silver(I) hexafluoroantimonate, (Z)-alkenylsilanes reacted with various carbon electrophiles (acetals, aminals, carboxylic anhydrides, alkyl chlorides, etc.) at the γ-position to give allylation products. A plausible mechanism for the platinum-catalyzed allylation involves alkene migration of alkenylsilanes to allylsilanes and subsequent allylation of carbon electrophiles, both of which are catalyzed by a cationic platinum(II) species.

Supporting Information

 
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