Synthesis 2017; 49(19): 4523-4534
DOI: 10.1055/s-0036-1589062
paper
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Catalyzed Alkyne Carbo- and Cycloalumination Reactions in Stereoselective Preparation of 1-Alkenyl Selenides

Rita N. Kadikova*
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
,
Ilfir R. Ramazanov
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
,
Alexey V. Vyatkin
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
,
Usein M. Dzhemilev
Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russian Federation   Email: kadikritan@gmail.com
› Author Affiliations
This work was supported by the Russian Foundation for Basic Research (Grant No. 16-33-60167 and 16-33-00403), which are gratefully acknowledged.
Further Information

Publication History

Received: 19 May 2017

Accepted after revision: 25 May 2017

Publication Date:
20 July 2017 (online)


Abstract

The Cp2ZrCl2-catalyzed methylalumination and сycloalumination of 1-alkynyl selenides followed by deuterolysis or hydrolysis affords corresponding (Z)-1-alkenyl selenides in high yields. Alternatively, (E)-1-alkenyl selenides were prepared by the reaction of 1-alkenylaluminums with organic diselenides in a one-pot procedure starting from the corresponding 1-alkynes, which provides a versatile tool for the preparation of stereo-defined unsaturated organic derivatives of selenium.

Supporting Information