Zhiyuan Tu, Jianan Zhan, Shengyong You, Mingzhong Cai
{"title":"可回收钯催化芳基卤化物和有机铝化合物与叔丁基异氰酸酯的羰基偶联反应,生成 1,2-二酮类化合物","authors":"Zhiyuan Tu, Jianan Zhan, Shengyong You, Mingzhong Cai","doi":"10.1055/s-0040-1720121","DOIUrl":null,"url":null,"abstract":"<p>An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using <i>tert</i>-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KO<sup>t</sup>Bu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones\",\"authors\":\"Zhiyuan Tu, Jianan Zhan, Shengyong You, Mingzhong Cai\",\"doi\":\"10.1055/s-0040-1720121\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using <i>tert</i>-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KO<sup>t</sup>Bu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.</p> \",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-06-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/s-0040-1720121\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/s-0040-1720121","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Recyclable Palladium-Catalyzed Carbonylative Coupling of Aryl Halides and Organoaluminum Compounds with tert-Butyl Isocyanide as CO Equivalent Leading to 1,2-Diketones
An efficient heterogeneous palladium-catalyzed carbonylative coupling of aryl halides and organoaluminum compounds has been developed using tert-butyl isocyanide as CO equivalent. The carbonylation reaction proceeds smoothly in toluene with KOtBu as a base at 100 °C by using 10 mol% of an SBA-15-anchored bidentate phosphine palladium(0) complex [2P-SBA-15-Pd(0)] as the catalyst and provides a general and practical approach for the assembly of 1,2-diketones in good to excellent yields. This heterogenized palladium catalyst can be readily separated and recovered via a simple centrifugation process and reused for more than seven cycles with almost consistent catalytic efficiency.