Issue 8, 2014

Synthesis and applications of 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides

Abstract

Selective I/Mg exchange reactions of 1,4-diiodo-1,3-dienes and o-iodo-2-(2-iodovinyl)benzenes were achieved viaiPrMgCl·LiCl. Various 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides were thus efficiently generated and synthetically applied to afford new C–C bonds via reactions of the alkenyl or aryl C–MgCl bonds with different electrophiles. Useful conjugated compounds including polysubstituted benzenes, naphthalenes and phosphine compounds could be synthesized readily via further applications of the remaining alkenyl C–I bonds and subsequent cyclization reactions.

Graphical abstract: Synthesis and applications of 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jul 2014
Accepted
04 Aug 2014
First published
08 Aug 2014

Org. Chem. Front., 2014,1, 983-987

Author version available

Synthesis and applications of 1-iodo-4-MgCl-1,3-dienes and 1-iodovinyl phenylmagnesium chlorides

J. Wei, Y. Zhang, W. Zhang and Z. Xi, Org. Chem. Front., 2014, 1, 983 DOI: 10.1039/C4QO00191E

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