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

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タイトル: Iridium(I)-catalyzed C-H Borylation of alpha,beta-Unsaturated Esters with Bis(pinacolato)diboron
著者: Sasaki, Ikuo 著作を一覧する
Taguchi, Jumpei 著作を一覧する
Doi, Hana 著作を一覧する
Ito, Hajime 著作を一覧する
Ishiyama, Tatsuo 著作を一覧する
キーワード: alkenyl boronates
borylation
diboron
iridium
alpha,beta-unsaturated esters
発行日: 2016年 5月 7日
出版者: Wiley-Blackwell
誌名: Chemistry-an asian journal
巻: 11
号: 9
開始ページ: 1400
終了ページ: 1405
出版社 DOI: 10.1002/asia.201600078
抄録: 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
資料タイプ: article (author version)
URI: http://hdl.handle.net/2115/65211
出現コレクション:雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

提供者: 石山 竜生

 

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