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Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility
| Title: | Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility |
| Authors: | Ishiyama, Tatsuo Browse this author →KAKEN DB | | Takagi, Jun Browse this author | | Kamon, Akihiro Browse this author | | Miyaura, Norio Browse this author →KAKEN DB |
| Keywords: | Bis(pinacolato)diboron | | Vinyl triflate | | Palladium catalyst | | Vinylboronate | | Cross-coupling |
| Issue Date: | 7-Dec-2003 |
| Publisher: | Elsevier |
| Journal Title: | Journal of Organometallic Chemistry |
| Volume: | 687 |
| Issue: | 2 |
| Start Page: | 284 |
| End Page: | 290 |
| Publisher DOI: | 10.1016/S0022-328X(03)00611-9 |
| Abstract: | Cross-coupling reaction of bis(pinacolato)diboron with β-(trifluoromethanesulfonyloxy)-α,β-unsaturated carbonyl compounds was carried out in the presence of PdCl2(PPh3)2-2PPh3 (3 mol%) and KOPh in toluene or K2CO3 in dioxane for the synthesis of cyclic and acyclic β-boryl-α,β-unsaturated esters, amides, and ketones in high yields. The vinylboronates thus obtained readily participated in carbon-carbon bond formation, such as cross-coupling with vinyl triflates and 1,4-addition to α,β-unsaturated ketones. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/56318 |
| 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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