Department of Chemistry,
and Shanghai Key Lab of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China
and Shanghai Key Lab of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China
Org. Lett., 2016, 18 (9), pp 2130–2133
DOI: 10.1021/acs.orglett.6b00753
Publication Date (Web): April 26, 2016
Copyright © 2016 American Chemical Society
*E-mail: zhangyanghui@tongji.edu.cn
Abstract
A
novel sequential difunctionalization reaction of 2-iodobiphenyl has
been developed by exploiting the distinct reactivities of a palladacycle
and an acyclic arylpalladium species. In this tandem reaction, an in
situ formed dibenzopalladacyclopentadiene reacts selectively with an
alkyl halide, after which the thus formed acyclic arylpalladium species
selectively undergoes a Heck reaction with an alkene. This work
demonstrates the strong relationship between the coordination mode of a
transition metal complex and its reactivity, which could shed light on
the mechanisms of other transition-metal-catalyzed reactions and offer
the opportunity to develop other synthetically enabling organic
transformations.
novel sequential difunctionalization reaction of 2-iodobiphenyl has
been developed by exploiting the distinct reactivities of a palladacycle
and an acyclic arylpalladium species. In this tandem reaction, an in
situ formed dibenzopalladacyclopentadiene reacts selectively with an
alkyl halide, after which the thus formed acyclic arylpalladium species
selectively undergoes a Heck reaction with an alkene. This work
demonstrates the strong relationship between the coordination mode of a
transition metal complex and its reactivity, which could shed light on
the mechanisms of other transition-metal-catalyzed reactions and offer
the opportunity to develop other synthetically enabling organic
transformations.
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