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The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides
| Title: | The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides |
| Authors: | Ishiyama, Tatsuo Browse this author →KAKEN DB | | Mori, Masashi Browse this author | | Suzuki, Akira Browse this author →KAKEN DB | | Miyaura, Norio Browse this author →KAKEN DB |
| Keywords: | Boron | | Palladium |
| Issue Date: | 15-Nov-1996 |
| Publisher: | Elsevier |
| Journal Title: | Journal of Organometallic Chemistry |
| Volume: | 525 |
| Issue: | 1-2 |
| Start Page: | 225 |
| End Page: | 231 |
| Publisher DOI: | 10.1016/S0022-328X(96)06495-9 |
| Abstract: | The synthesis of unsymmetrical sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of 9-organothio-9-bombicyclo[3.3. l]nonane (9-RS-9-BBN) with organic electrophiles, such as iodoarenes, i-iodo-I-alkenes, allyl carbonate and propargyl carbonate, lodoarenes and I-iodo-l-alkenes were smoothly converted into the corresponding sulfides at 50°C in the presence of PdCi_~(dppO (3 tool%) and K 3PO4 (3 equiv.) in DMF. in contrast, the cross-coupling reaction of 9-RS-9-BBN with allyl or propargyl carbonates occurred in DMF without the assistance of a base. Both reactions ~. :talyzed by Pd(dba)z-dppf regioselectively produced allyl and allenyl sulfides in excellent yields. The scope and limitations of the reactions, as well as the effects of varying the ~action conditions, are discussed. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/56159 |
| 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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