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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摘要：

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 3 PO 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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关键词：

mercaptans, thioethers (benzene compounds catalysis, phase‐transfer catalysis sulfuration, desulfuration, sulfonation, desulfonation

DOI：

10.1016/S0022-328X(96)06495-9

被引量：

242

年份：

1997