Catalyst-free hydroarylation of in situ generated ortho-quinone methide (o-QM) with electron rich arenes in water

作者: Atul Kumar , Mukesh Kumar , Maneesh Kumar Gupta

DOI: 10.1039/C2GC35741K

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摘要: We report the first C–H hydroarylation of in situ generated ortho-quinone methides with electron-rich arenes. The reaction takes place water without any catalyst, and is highly regioselective. Ionic non-ionic additives provide an increase rate, yield, regioselectivity.

参考文章(75)
Raphaël Rodriguez, Robert M. Adlington, John E. Moses, Andrew Cowley, Jack E. Baldwin, A New and Efficient Method for o-Quinone Methide Intermediate Generation: Application to the Biomimetic Synthesis of (±)-Alboatrin Organic Letters. ,vol. 6, pp. 3617- 3619 ,(2004) , 10.1021/OL048479D
Hongming Wang, Yong Wang, Ke-Li Han, Xiao-Jun Peng, A DFT study of Diels-Alder reactions of o-quinone methides and various substituted ethenes: selectivity and reaction mechanism. Journal of Organic Chemistry. ,vol. 70, pp. 4910- 4917 ,(2005) , 10.1021/JO0479213
Pengfei Wang, Mukulesh Mondal, Yun Wang, Photolabile Carbonyl Protecting Group: A New Tool for Light‐Controlled Release of Anticancer Agents European Journal of Organic Chemistry. ,vol. 2009, pp. 2055- 2058 ,(2009) , 10.1002/EJOC.200900093
Phillip. J. Black, Gerta Cami-Kobeci, Michael G. Edwards, Paul A. Slatford, Michael K. Whittlesey, Jonathan M. J. Williams, Borrowing hydrogen: iridium-catalysed reactions for the formation of C–C bonds from alcohols Organic and Biomolecular Chemistry. ,vol. 4, pp. 116- 125 ,(2006) , 10.1039/B511053J
Ranjan Jana, Jon A. Tunge, A Homogeneous, Recyclable Rhodium(I) Catalyst for the Hydroarylation of Michael Acceptors Organic Letters. ,vol. 11, pp. 971- 974 ,(2009) , 10.1021/OL802927V
Jung Ho Do, Ha Na Kim, Juyoung Yoon, Jong Seung Kim, Hae-Jo Kim, A Rationally Designed Fluorescence Turn-On Probe for the Gold(III) Ion Organic Letters. ,vol. 12, pp. 932- 934 ,(2010) , 10.1021/OL902860F
Philip Norcott, Calan Spielman, Christopher S. P. McErlean, An in-water, on-water domino process for synthesis Green Chemistry. ,vol. 14, pp. 605- 609 ,(2012) , 10.1039/C2GC16259H