The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides
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The synthesis of unsymmetrical sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of9-organothio-9-bombicyclo[3.3. l]nonane (9-RS-9-BBN) with organic electrophiles, such as iodoarenes, i-iodo-I-alkenes, allyl carbonateand propargyl carbonate, lodoarenes and I-iodo-l-alkenes were smoothly converted into the corresponding sulfides at 50°C in thepresence 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 orpropargyl carbonates occurred in DMF without the assistance of a base. Both reactions ~. :talyzed by Pd(dba)z-dppf regioselectivelyproduced 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.
- Elsevierの論文
- 1996-11-15
Elsevier | 論文
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