open access

https://hdl.handle.net/2115/65211

Iridium(I)-catalyzed C-H Borylation of alpha,beta-Unsaturated Esters with Bis(pinacolato)diboron

英語

alpha,beta-unsaturated esters

2016-05-07

Wiley-Blackwell

Chemistry-an asian journal

11(9)

1400-1405

A new process has been developed for the iridium(I)-catalyzed vinylic C-H borylation of alpha,beta-unsaturated esters with bis(pinacolato) diboron (B(2)pin(2)). These reactions proceeded in octane at temperatures in the range of 80-120 degrees C to afford the corresponding alkenylboronic compounds in high yields with excellent regio- and stereoselectivities. The presence of an aryl ester led to significant improvements in the yields of the acyclic alkenylboronates. Crossover experiments involving deuterated substrates as well as a mixture of stereoisomers confirmed that this reaction proceeds via a 1,4-addition/beta-hydride elimination mechanism. Notably, this reaction was also used to develop a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.

学術雑誌論文

Accepted Manuscript

This is the accepted version of the following article: Chemistry-an asian journal, 11(9), 1400-1405, 2016, which has been published in final form at http://doi.org/10.1002/asia.201600078. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy http://olabout.wiley.com/WileyCDA/Section/id-828039.html

1861-4728