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

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Title: Iridium(I)-catalyzed C-H Borylation of alpha,beta-Unsaturated Esters with Bis(pinacolato)diboron
Authors: Sasaki, Ikuo Browse this author
Taguchi, Jumpei Browse this author
Doi, Hana Browse this author
Ito, Hajime Browse this author →KAKEN DB
Ishiyama, Tatsuo Browse this author →KAKEN DB
Keywords: alkenyl boronates
borylation
diboron
iridium
alpha,beta-unsaturated esters
Issue Date: 7-May-2016
Publisher: Wiley-Blackwell
Journal Title: Chemistry-an asian journal
Volume: 11
Issue: 9
Start Page: 1400
End Page: 1405
Publisher DOI: 10.1002/asia.201600078
PMID: 26929021
Abstract: 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.
Rights: 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
Type: article (author version)
URI: http://hdl.handle.net/2115/65211
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 石山 竜生

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