Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal
Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal
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DOI：
10.1021/jo801074g
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发表时间：
2008-09-19
影响因子：
3.6
通讯作者：
Minehan, Thomas
中科院分区：
文献类型：
--
作者：
Papoian, Vardan;Minehan, Thomas
在氯化锂存在下，芳基碘化物与金属铟反应生成一种能够参与过渡金属催化下的交叉偶联反应的有机铟试剂。在5mol%Cl2Pd(Dppf)存在下与芳基卤化物反应，以很好的产率提供联芳基化合物；类似地，在5-10mol%钯催化剂存在下，与酰基卤化物或烯丙基乙酸酯/碳酸盐反应，分别以中等产率生成芳基酮和烯丙基取代产物。该反应耐受质子性溶剂的存在，用锌(0)还原残留的铟盐可回收约85%的金属铟。
Treatment of aryl iodides with indium metal in the presence of lithium chloride leads to the formation of an organoindium reagent capable of participating in cross-coupling reactions under transition-metal catalysis. Combination with aryl halides in the presence of 5 mol % Cl2Pd(dppf) furnishes biaryl compounds in good yields; similarly, reaction with acyl halides or allylic acetates/carbonates in the presence of 5-10 mol % palladium catalyst leads to arylketones and allylic substitution products, respectively, in moderate yields. The reactions are tolerant of the presence of protic solvents, and similar to 85% of the indium metal employed can be recovered by reduction of the residual indium salts with zinc(0).