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Iridium(I)-catalyzed C-H Borylation of alpha,beta-Unsaturated Esters with Bis(pinacolato)diboron
| 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)
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Submitter: 石山 竜生
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