Copper-catalyzed direct synthesis of furans and thiophenes via decarboxylative coupling of alkynyl carboxylic acids with H2O or Na2S
作者： Francis Mariaraj Irudayanathan , Gabriel Charles Edwin Raja , Sunwoo Lee
DOI: 10.1016/J.TET.2015.05.017
关键词: Aryl 、 Copper catalyzed 、 Yield (chemistry) 、 Catalysis 、 Chemistry 、 Thiophene 、 Copper 、 Furan 、 Organic chemistry 、 Ligand
摘要: 2,5-Diaryl-substituted furans were synthesized from the copper-catalyzed decarboxylative coupling of aryl-substituted aryl propiolic acids in presence H2O. The homocoupling alkynyl carboxylic provided 1,4-diaryldiynes, which then reacted with H2O to give desired through cyclization. Addition copper catalyst was critical, and addition a ligand increased yield products both cyclization reactions. In addition, thiophenes could be obtained when reaction conducted Na2S.
sci-hub.se 参考文章(40)
Kyungho Park, Jung-Min You, Seungwon Jeon, Sunwoo Lee, Palladium‐Catalyzed Sonogashira Reaction for the Synthesis of Arylalkynecarboxylic Acids from Aryl Bromides at Low Temperature European Journal of Organic Chemistry. ,vol. 2013, pp. 1973- 1978 ,(2013) , 10.1002/EJOC.201201606
Andrej Kolarovič, Zuzana Fáberová, Catalytic Decarboxylation of 2-Alkynoic Acids Journal of Organic Chemistry. ,vol. 74, pp. 7199- 7202 ,(2009) , 10.1021/JO901377B
Hyunseok Kim, Phil Ho Lee, Palladium‐Catalyzed Decarboxylative sp‐sp2 Cross‐Coupling Reactions of Aryl and Vinyl Halides and Triflates with α,β‐Ynoic Acids using Silver Oxide Advanced Synthesis & Catalysis. ,vol. 351, pp. 2827- 2832 ,(2009) , 10.1002/ADSC.200900502
Thiruvengadam Palani, Kyungho Park, Manian Rajesh Kumar, Hyun Ming Jung, Sunwoo Lee, Copper‐Catalyzed Decarboxylative Three‐Component Reactions for the Synthesis of Imidazo[1,2‐a]pyridines European Journal of Organic Chemistry. ,vol. 2012, pp. 5038- 5047 ,(2012) , 10.1002/EJOC.201200679
Venkataraman Amarnath, Kalyani Amarnath, Intermediates in the Paal-Knorr Synthesis of Furans Journal of Organic Chemistry. ,vol. 60, pp. 301- 307 ,(1995) , 10.1021/JO00107A006
Jeongju Moon, Miso Jeong, Hyungoog Nam, Jinhun Ju, Joong Ho Moon, Hyun Min Jung, Sunwoo Lee, One-Pot Synthesis of Diarylalkynes Using Palladium-Catalyzed Sonogashira Reaction and Decarboxylative Coupling of sp Carbon and sp2 Carbon Organic Letters. ,vol. 10, pp. 945- 948 ,(2008) , 10.1021/OL703130Y
Sadananda Ranjit, Zhongyu Duan, Pengfei Zhang, Xiaogang Liu, Synthesis of vinyl sulfides by copper-catalyzed decarboxylative C-S cross-coupling. Organic Letters. ,vol. 12, pp. 4134- 4136 ,(2010) , 10.1021/OL101729K
Wei Jia, Ning Jiao, Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling. Organic Letters. ,vol. 12, pp. 2000- 2003 ,(2010) , 10.1021/OL1004615
Manian Rajesh Kumar, Francis Mariaraj Irudayanathan, Joong Ho Moon, Sunwoo Lee, Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control Advanced Synthesis & Catalysis. ,vol. 355, pp. 3221- 3230 ,(2013) , 10.1002/ADSC.201300561
Kyungho Park, Goun Bae, Jeongju Moon, Jaehoon Choe, Kwang Ho Song, Sunwoo Lee, Synthesis of Symmetrical and Unsymmetrical Diarylalkynes from Propiolic Acid Using Palladium-Catalyzed Decarboxylative Coupling Journal of Organic Chemistry. ,vol. 75, pp. 6244- 6251 ,(2010) , 10.1021/JO101398A