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Chemistry of Group 13 element-transition metal linkage — the platinum- and palladium-catalyzed reactions of (alkoxo)diborons
| Title: | Chemistry of Group 13 element-transition metal linkage — the platinum- and palladium-catalyzed reactions of (alkoxo)diborons |
| Authors: | Ishiyama, Tatsuo Browse this author →KAKEN DB | | Miyaura, Norio Browse this author →KAKEN DB |
| Keywords: | Metal-catalyzed reaction | | Diboran(4) | | Palladium | | Platinum | | Rhodium | | Cross-coupling | | Diboration | | Organoboron compound |
| Issue Date: | 6-Oct-2000 |
| Publisher: | Elsevier |
| Journal Title: | Journal of Organometallic Chemistry |
| Volume: | 611 |
| Issue: | 1-2 |
| Start Page: | 392 |
| End Page: | 402 |
| Publisher DOI: | 10.1016/S0022-328X(00)00470-8 |
| Abstract: | The metal-catalyzed borylation of alkenes, alkynes, and organic electrophiles with B B compounds was developed for the synthesis of organoboronic esters from simple organic substrates. The platinum(0)-catalyzed addition of bis(pinacolato)diboron to alkenes and alkynes stereoselectively yielded cis-bis(boryl)alkanes or cis-bis(boryl)alkenes. The addition of diboron to 1,3-dienes with a platinum(0) complex afforded a new access to the cis-1,4-bis(boryl)butene derivatives which are a versatile reagent for diastereoselective allylboration of carbonyl compounds. The cross-coupling reaction of diborons with aryl and vinyl halides or triflates, and allyl chlorides or acetates was found to yield aryl-, vinyl-, and allylboronates in high yields in the presence of a base and a palladium catalyst, which provides the first one-step procedure for the synthesis of organoboronic esters from organic electrophiles. The mechanisms and the synthetic applications of these reactions are discussed. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/56476 |
| 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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