Pd‐Catalyzed Tandem Chemoselective Synthesis of 2‐Arylbenzofurans using Threefold Arylating Triarylbismuth Reagents

作者: Maddali L. N. Rao , Deepak N. Jadhav , Priyabrata Dasgupta

DOI: 10.1002/EJOC.201201314

关键词:

摘要: A tandem chemoselective synthesis of 2-arylbenzofurans was accomplished from o-hydroxy-gem-(dibromovinyl)benzenes and BiAr3 reagents under palladium-catalyzed conditions. This unique synthetically valuable strategy proceeds through three consecutive coupling reactions involving triarylbismuth provides 2-arylbenzofuran products in high yields.

参考文章(59)
Derek H.R. Barton, Nubar Ozbalik, Manian Ramesh, The chemistry of orqanobismuth reagents: Part XIII ligand coupling induced by Pd(O) Tetrahedron. ,vol. 44, pp. 5661- 5668 ,(1988) , 10.1016/S0040-4020(01)81427-7
Xurong Qin, Xuefeng Cong, Dongbing Zhao, Jingsong You, Jingbo Lan, One-pot synthesis of benzofused heteroaryl azoles via tandem C-heteroatom coupling/C–H activation of azoles Chemical Communications. ,vol. 47, pp. 5611- 5613 ,(2011) , 10.1039/C1CC10572H
Giorgio Chelucci, Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems Chemical Reviews. ,vol. 112, pp. 1344- 1462 ,(2012) , 10.1021/CR200165Q
Wei Zhou, Wei Chen, Lei Wang, A highly efficient one-pot reaction of 2-(gem-dibromovinyl)phenols(thiophenols) with K4Fe(CN)6 to 2-cyanobenzofurans(thiophenes) Organic and Biomolecular Chemistry. ,vol. 10, pp. 4172- 4178 ,(2012) , 10.1039/C2OB25356A
James J. La Clair, Arnold L. Rheingold, Michael D. Burkart, Ganodone, a bioactive benzofuran from the fruiting bodies of Ganoderma tsugae. Journal of Natural Products. ,vol. 74, pp. 2045- 2051 ,(2011) , 10.1021/NP200361Y
Christopher S. Bryan, Mark Lautens, Stephen G. Newman, Valentina Aureggi, Intramolecular cross-coupling of gem-dibromoolefins: a mild approach to 2-bromo benzofused heterocycles Chemical Communications. pp. 5236- 5238 ,(2009) , 10.1039/B912093A
Xin-Fang Duan, Jing Zeng, Zhan-Bin Zhang, Guo-Fu Zi, A Facile Two-Step Synthesis of 2-Arylbenzofurans Based on the Selective Cross McMurry Couplings Journal of Organic Chemistry. ,vol. 72, pp. 10283- 10286 ,(2007) , 10.1021/JO7019652
Michael C. Willis, Dawn Taylor, Adam T. Gillmore, Palladium-Catalyzed IntramolecularO-Arylation of Enolates:  Application to Benzo[b]furan Synthesis Organic Letters. ,vol. 6, pp. 4755- 4757 ,(2004) , 10.1021/OL047993G
Maddali L. N. Rao, Deepak N. Jadhav, Varadhachari Venkatesh, Atom‐Efficient Vinylic Arylations with Triarylbismuths as Substoichiometric Multicoupling Reagents under Palladium Catalysis European Journal of Organic Chemistry. ,vol. 2009, pp. 4300- 4306 ,(2009) , 10.1002/EJOC.200900487
Gary A. Molander, Belgin Canturk, Lauren E. Kennedy, Scope of the Suzuki-Miyaura Cross-Coupling Reactions of Potassium Heteroaryltrifluoroborates Journal of Organic Chemistry. ,vol. 74, pp. 973- 980 ,(2009) , 10.1021/JO802590B