Abstract
The synthesis of unsymmetrical sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonane (9-RS-9-BBN) with organic electrophiles, such as iodoarenes, l-iodo-l-alkenes, allyl carbonate and propargyl carbonate. Iodoarenes and l-iodo-l-alkenes were smoothly converted into the corresponding sulfides at 50°C in the presence of PdCl 2((dppf) 3 mol%) and K 3PO 4 (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 reactionscatalyzed by Pd(dba) 2-dppf regioselectively produced allyl and allenyl sulfides in excellent yields. The scope and limitationsof the reactions, as well as the effects of varying the reaction conditions, are discussed.
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