Synthesis of functionalized alkyl substituted benzoquinones by Rh-catalyzed additions of boronic acids

作者: Marcos Veguillas , Jaime Rojas-Martín , María Ribagorda , M. Carmen Carreño

DOI: 10.1039/C7OB00979H

关键词:

摘要: A general synthetic route to γ-oxo alkyl or α-hydroxy benzyl 2-substituted benzoquinones has been developed through a one-pot Rh-catalyzed C–C bond formation/oxidative demethylation sequence from 2,5-dimethoxy aryl boronic acids and several electron deficient alkenes aldehydes. The process allows rapid access functionalized under very mild conditions good yields. We disclose the first example of 1,4-addition reaction benzoquinonyl acid methyl vinyl ketone other conjugate acceptors, which direct synthesis 2-(γ-functionalized alkyl) substituted benzoquinones.

参考文章(81)
Łukasz Albrecht, Clarisa Villegas Gómez, Christian Borch Jacobsen, Karl Anker Jørgensen, 1,4-Naphthoquinones in H-Bond-Directed Trienamine-Mediated Strategies Organic Letters. ,vol. 15, pp. 3010- 3013 ,(2013) , 10.1021/OL401204A
Gary A. Molander, Organotrifluoroborates: Another Branch of the Mighty Oak Journal of Organic Chemistry. ,vol. 80, pp. 7837- 7848 ,(2015) , 10.1021/ACS.JOC.5B00981
Xiao-Le Zhou, Pu-Sheng Wang, Da-Wei Zhang, Peng Liu, Cheng-Ming Wang, Liu-Zhu Gong, Enantioselective Functionalization of Inactive sp(3) C-H Bonds Remote to Functional Group by Metal/Organo Cooperative Catalysis. Organic Letters. ,vol. 17, pp. 5120- 5123 ,(2015) , 10.1021/ACS.ORGLETT.5B02653
Ming Yan, Julian C. Lo, Jacob T. Edwards, Phil S. Baran, Radicals: Reactive Intermediates with Translational Potential Journal of the American Chemical Society. ,vol. 138, pp. 12692- 12714 ,(2016) , 10.1021/JACS.6B08856
Judy L. Bolton, Tareisha Dunlap, Formation and Biological Targets of Quinones: Cytotoxic versus Cytoprotective Effects Chemical Research in Toxicology. ,vol. 30, pp. 13- 37 ,(2017) , 10.1021/ACS.CHEMRESTOX.6B00256
Gongming Zhu, Guangjun Bao, Yiping Li, Junxian Yang, Wangsheng Sun, Jing Li, Liang Hong, Rui Wang, Chiral Phosphoric Acid Catalyzed Asymmetric Oxidative Dearomatization of Naphthols with Quinones Organic Letters. ,vol. 18, pp. 5288- 5291 ,(2016) , 10.1021/ACS.ORGLETT.6B02609
José Alemán, Bo Richter, Karl Anker Jørgensen, Organocatalytic Highly enantioselective alpha-arylation of beta-ketoesters. Angewandte Chemie. ,vol. 46, pp. 5515- ,(2007) , 10.1002/ANIE.200701009
Jose Marco-Contelles, Maria Molina, Naturally Occurring Diazo Compounds: The Kinamycins Current Organic Chemistry. ,vol. 7, pp. 1433- 1442 ,(2003) , 10.2174/1385272033486396
Mathieu Pucheault, Sylvain Darses, Jean-Pierre Genêt, Potassium Organotrifluoroborates in Rhodium-Catalyzed Asymmetric 1,4-Additions to Enones European Journal of Organic Chemistry. ,vol. 2002, pp. 3552- 3557 ,(2002) , 10.1002/1099-0690(200211)2002:21<3552::AID-EJOC3552>3.0.CO;2-4