Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

Bin Wang; Yihang Li; Jia Hao Pang; Kohei Watanabe; Ryo Takita; Shunsuke Chiba

doi:10.1002/anie.202012027

Hydromagnesiation of 1,3-Enynes by Magnesium Hydride for Synthesis of Tri- and Tetra-substituted Allenes

Angew Chem Int Ed Engl. 2021 Jan 4;60(1):217-221. doi: 10.1002/anie.202012027. Epub 2020 Nov 3.

Authors

Bin Wang¹, Yihang Li¹, Jia Hao Pang¹, Kohei Watanabe², Ryo Takita², Shunsuke Chiba¹

Affiliations

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
² Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.

PMID: 32936502
DOI: 10.1002/anie.202012027

Abstract

A protocol for regio-controlled hydromagnesiation of 1,3-enynes was developed using magnesium hydride that is generated in situ by solvothermal treatment of sodium hydride (NaH) and magnesium iodide (MgI₂ ) in THF. The resulting allenylmagnesium species could be converted into tri- and tetra-substituted allenes by subsequent treatment with various carbon- and silicon-based electrophiles with the aid of CuCN as a catalyst.

Keywords: allenes; enynes; hydromagnesiation; magnesium hydride; sodium hydride.

Publication types

Research Support, Non-U.S. Gov't