Papoian Vardan, Minehan Thomas
Department of Chemistry and Biochemistry, California State University-Northridge, Northridge, California 91330, USA.
J Org Chem. 2008 Sep 19;73(18):7376-9. doi: 10.1021/jo801074g. Epub 2008 Aug 22.
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 approximately 85% of the indium metal employed can be recovered by reduction of the residual indium salts with zinc(0).
在氯化锂存在下，用铟金属处理芳基碘化物会生成一种有机铟试剂，该试剂能够在过渡金属催化下参与交叉偶联反应。在5 mol%的二氯双(二苯基膦)钯(Cl2Pd(dppf))存在下与芳基卤化物结合，能以良好的产率得到联芳基化合物；类似地，在5 - 10 mol%钯催化剂存在下与酰卤或烯丙基乙酸酯/碳酸酯反应，分别以中等产率得到芳基酮和烯丙基取代产物。这些反应能耐受质子性溶剂的存在，并且通过用零价锌还原残留的铟盐，大约85%使用的铟金属可以回收。
