A facile and practical synthetic route of unsymmetrical 1,3-diynes via the PdC1/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3-（diphenylphosphino）propanoic acid as a...A facile and practical synthetic route of unsymmetrical 1,3-diynes via the PdC1/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3-（diphenylphosphino）propanoic acid as a ligand in the presence of oxygen. This system is suitable for not only aromatic alkynes but also heteroaromatic and aliphatic alkynes which were transformed into the corresponding unsymmetrical 1,3-diynes in moderate to good yields at room temperature. Moreover, the unsymmetrical 1,3-diynes were also obtained on a multi-gram scale. Mechanistic studies suggest that oxygen plays a key role in the catalytic cycles.展开更多
Synthesis of triarylmethanes via metal-free reductive coupling of diaryl ketone, tosylhydrazide, and arylboronic acids has been developed. This methodology is realized via one-pot two-step reactions involving the prep...Synthesis of triarylmethanes via metal-free reductive coupling of diaryl ketone, tosylhydrazide, and arylboronic acids has been developed. This methodology is realized via one-pot two-step reactions involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with diaryl ketone derivatives, followed by the reductive coupling with arylboronic acid in the presence of potassium carbonate to afford various triarylmethanes analogues in moder- ate to good yields. Importantly, the system presented here enables the use of easily accessible starting materials and a series of substrates with diverse functional group could be tolerant in this reaction. This approach could also be particularly useful for the synthesis of triaryl-substituted carbazolyl compounds.展开更多
基金We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China （Nos. 21563025, 21463022）, Shihezi University Training Programme for Distinguished Youth Scholars （No. 2014ZRKXJQ05）, and Start-Up Foundation for Young Scientists of Shihezi University （No. RCZX201408）.
文摘A facile and practical synthetic route of unsymmetrical 1,3-diynes via the PdC1/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3-（diphenylphosphino）propanoic acid as a ligand in the presence of oxygen. This system is suitable for not only aromatic alkynes but also heteroaromatic and aliphatic alkynes which were transformed into the corresponding unsymmetrical 1,3-diynes in moderate to good yields at room temperature. Moreover, the unsymmetrical 1,3-diynes were also obtained on a multi-gram scale. Mechanistic studies suggest that oxygen plays a key role in the catalytic cycles.
基金We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China （No. 21563025）, Shihezi University Training Programme for Distinguished Youth Scholars （No. 2014ZRKXJQ05）, and Start-Up Foundation for Young Scientists of Shihezi University （RCZX201408）.
文摘Synthesis of triarylmethanes via metal-free reductive coupling of diaryl ketone, tosylhydrazide, and arylboronic acids has been developed. This methodology is realized via one-pot two-step reactions involving the preparation of N-tosylhydrazones by reacting tosylhydrazide with diaryl ketone derivatives, followed by the reductive coupling with arylboronic acid in the presence of potassium carbonate to afford various triarylmethanes analogues in moder- ate to good yields. Importantly, the system presented here enables the use of easily accessible starting materials and a series of substrates with diverse functional group could be tolerant in this reaction. This approach could also be particularly useful for the synthesis of triaryl-substituted carbazolyl compounds.
