Ruthenium??Catalyzed Synthesis of Indoles from Anilines and Epoxides

M Peña??López, H Neumann…

Index: Pena-Lopez, Miguel; Neumann, Helfried; Beller, Matthias Chemistry - A European Journal, 2014 , vol. 20, # 7 p. 1818 - 1824

Full Text: HTML

Citation Number: 15

Abstract

Abstract A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru 3 (CO) 12]/1, 1′-bis (diphenylphosphino) ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by-products, making this process highly atom efficient.

~49%

~75%

~70%

~46%

~60%

~63%

~65%

~52%

~78%

~75%

~84%

~82%

~75%

~88%

~85%

~77%

~79%

Fischer indole synthesis in brønsted acidic ionic liquids: a...

[Xu, Dan-Qian; Yang, Wen-Long; Luo, Shu-Ping; Wang, Bing-Tao; Wu, Jian; Xu, Zhen-Yuan European Journal of Organic Chemistry, 2007 , # 6 p. 1007 - 1012]

Fischer indole synthesis in low melting mixtures

[Gore, Sangram; Baskaran, Sundarababu; Koenig, Burkhard Organic Letters, 2012 , vol. 14, # 17 p. 4568 - 4571]

Synthesis of Indoles via Palladium [0]-Mediated Ullmann Cros...

[Banwell, Martin G.; Kelly, Brian D.; Kokas, Okanya J.; Lupton, David W. Organic Letters, 2003 , vol. 5, # 14 p. 2497 - 2500]

Regiocontrolled Synthesis of Carbocycle-Fused Indoles via Ar...

[Iwama, Tetsuo; Birman, Vladimir B.; Kozmin, Sergey A.; Rawal, Viresh H. Organic Letters, 1999 , vol. 1, # 4 p. 673 - 676]

Photocycloaddition of dimethyl acetylenedicarboxylate to act...

[Davis, Paul D.; Neckers, Douglas C. Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 456 - 462]