Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages
碩士 === 國立成功大學 === 化學系碩博士班 === 95 === 1,2,3,4-Tetraphenylnaphthalene (33a) can be prepared from the reaction of triphenylphosphine and diphenylacetylene (31a) in the presence of the palladium catalyst. The catalytic efficiencies of several palladium complexes, the reactivity of phenylphosphine compou...
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ndltd-TW-095NCKU50650232015-10-13T14:16:09Z http://ndltd.ncl.edu.tw/handle/50246964861466319583 Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages 經由芳香環碳−磷鍵及碳−氫鍵斷裂合成1,2,3,4−四取代萘 Chien-chuan Shih 施建全 碩士 國立成功大學 化學系碩博士班 95 1,2,3,4-Tetraphenylnaphthalene (33a) can be prepared from the reaction of triphenylphosphine and diphenylacetylene (31a) in the presence of the palladium catalyst. The catalytic efficiencies of several palladium complexes, the reactivity of phenylphosphine compounds and the contributions from solvents and additives have been examined. The reaction conditions have been optimized: When the solution of triphenylphosphine and 31a in acetonitrile was added to our developed catalytic system by a syringe pump at 110 ℃, and 33a could be obtained in 62% yield. To our best knowledge, this is the first example for the preparation of naphthalenes via the activation of a phenyl C-P bonds and C-H bonds. Based on this synthetic method, five naphthalene derivatives have been prepared in 22-62% yields. 5,8-Dimethyl-1,2,3,4-tetraphenylnaphthalene (35a) can be accessible directly from p-xylene and 31a under the catalysis of palladium acetate. This protocol provides three obvious advantages: simple, clean and atomic economics. From the structure of 35, an arene offers a〝benzo〞unit to construct a naphthalene core via double aryl C-H activations. Our coworker has optimized the reaction conditions. Based on the procedure, four highly substituted naphthalenes 35ab, 35ac, 35bb and 35cc have been prepared in 22-45% yields. Yao-ting Wu 吳耀庭 2007 學位論文 ; thesis 62 zh-TW |
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碩士 === 國立成功大學 === 化學系碩博士班 === 95 === 1,2,3,4-Tetraphenylnaphthalene (33a) can be prepared from the reaction of triphenylphosphine and diphenylacetylene (31a) in the presence of the palladium catalyst. The catalytic efficiencies of several palladium complexes, the reactivity of phenylphosphine compounds and the
contributions from solvents and additives have been examined. The reaction conditions have been optimized: When the solution of triphenylphosphine and 31a in acetonitrile was added to our developed catalytic system by a syringe pump at 110 ℃, and 33a could be obtained in 62% yield. To our best knowledge, this is the first example for the preparation of naphthalenes via the activation of a phenyl C-P bonds and C-H bonds. Based on this synthetic method, five naphthalene derivatives have been prepared in 22-62% yields.
5,8-Dimethyl-1,2,3,4-tetraphenylnaphthalene (35a) can be accessible directly from p-xylene and 31a under the catalysis of palladium acetate. This protocol provides three obvious advantages: simple, clean and atomic economics. From the structure of 35, an arene offers a〝benzo〞unit to construct a naphthalene core via double aryl C-H activations. Our coworker has optimized the reaction conditions. Based on the procedure, four highly substituted naphthalenes 35ab, 35ac, 35bb and 35cc have been prepared in 22-45% yields.
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author2 |
Yao-ting Wu |
author_facet |
Yao-ting Wu Chien-chuan Shih 施建全 |
author |
Chien-chuan Shih 施建全 |
spellingShingle |
Chien-chuan Shih 施建全 Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages |
author_sort |
Chien-chuan Shih |
title |
Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages |
title_short |
Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages |
title_full |
Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages |
title_fullStr |
Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages |
title_full_unstemmed |
Synthesis of 1,2,3,4−Tetrasubstituted Naphthalenesvia a aryl C−P Bond and a C−H Bond Cleavages |
title_sort |
synthesis of 1,2,3,4−tetrasubstituted naphthalenesvia a aryl c−p bond and a c−h bond cleavages |
publishDate |
2007 |
url |
http://ndltd.ncl.edu.tw/handle/50246964861466319583 |
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