https://scholars.lib.ntu.edu.tw/handle/123456789/626389
標題: | Unexpected hydrodeiodo Sonogashira-Heck-Casser coupling reaction of 2,2′-diiodobiphenyls with acetylenes | 作者: | Chou M.-Y Mandal A.B MAN-KIT LEUNG |
公開日期: | 2002 | 卷: | 67 | 期: | 5 | 起(迄)頁: | 1501-1505 | 來源出版物: | Journal of Organic Chemistry | 摘要: | 2,2′-Diiodobiphenyl-4,4′-dicarboxylic acid dimethyl ester (3) undergoes either a ring-closure reaction with phenylacetylene to give 4 or hydrodeiodo phenylethynylation to give 5 under the catalytic conditions of Pd(OAc)2/CuI/phosphine in amines. In these reactions, the amine and the phosphine ligands play important roles in controlling the reactivity. Among the ligands we used, tris(o-tolyl)phosphine is the best ligand for hydrodeiodo phenylethynylation, while the bidentate phosphine ligand retards both of the reactions. On the basis of our results, we propose that 5 is formed through a fast hydrodeiodination, followed by a Sonogashira phenylethynylation. The results of the deuterium labeling experiments show that proton exchange between the acetylenic proton and the alkyl protons of amine occurs effectively under the reaction conditions. In addition, the hydrogen that replaces the iodide in the hydrodeiodination process arises mainly from the acetylenic proton. |
URI: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037040650&doi=10.1021%2fjo010862y&partnerID=40&md5=60e78e291a9539b698c61815ae292450 https://scholars.lib.ntu.edu.tw/handle/123456789/626389 |
ISSN: | 00223263 | DOI: | 10.1021/jo010862y | SDG/關鍵字: | Ring-closure reaction; Amines; Catalysis; Deuterium; Esters; Ion exchange; Protons; Acetylene; 2,2' diiodobiphenyl 4,4' dicarboxylic acid dimethyl ester; 2,2' diiodobiphenyl derivative; acetylene derivative; biphenyl derivative; dimethyl 2 phenylethynylbiphenyl 4,4' dicarboxylate; unclassified drug; alkylation; article; cyclization; iodination; proton nuclear magnetic resonance; reaction analysis; stereospecificity; stoichiometry |
顯示於: | 化學系 |
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