Synlett 2018; 29(06): 727-730
DOI: 10.1055/s-0036-1591511
cluster
© Georg Thieme Verlag Stuttgart · New York

Activation of a Carbon–Carbon Bond in Internal Alkynes: Vinylidene Rearrangement of Disubstituted Alkynes at an Ir Complex

Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Shuhei Takamori
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Satoshi Kishi
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Takahiro Watanabe
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Yousuke Ikeda
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Shintaro Kodama
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Yasunori Minami
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
,
Youichi Ishii*
Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan   Email: yo-ishii@kc.chuo-u.ac.jp
› Author Affiliations
This research was supported financially by JST ACT-C (No. JPMJCR12Z1).
Further Information

Publication History

Received: 04 September 2017

Accepted after revision: 04 October 2017

Publication Date:
26 October 2017 (online)


Published as part of the Cluster C–C Activation

Abstract

Reactions of [Cp*Ir(PPh3)Cl2] with various internal acyl­alkynes in the presence of NaBArF 4 resulted in the selective formation of iridacycles via vinylidene rearrangement. 13C-labeling experiments revealed that the acyl group selectively migrates to the other acetylenic carbon atom. This trend is the same as that in the vinylidene rearrangement of internal alkynes at a group 8 metal center.

Supporting Information

 
  • References and Notes

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