Mild and Efficient One-Pot Synthesis of 2-(Perfluoroalkyl)indoles by Means of Sequential Michael-Type Addition and Pd(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) Reaction

Dandan Shen; Jing Han; Jie Chen; Hongmei Deng; Min Shao; Hui Zhang; Weiguo Cao

doi:10.1021/acs.orglett.5b01479

Mild and Efficient One-Pot Synthesis of 2-(Perfluoroalkyl)indoles by Means of Sequential Michael-Type Addition and Pd(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) Reaction

Org Lett. 2015 Jul 2;17(13):3283-5. doi: 10.1021/acs.orglett.5b01479. Epub 2015 Jun 19.

Authors

Dandan Shen¹, Jing Han¹, Jie Chen¹, Hongmei Deng², Min Shao², Hui Zhang^{1

2}, Weiguo Cao^{1

3

4}

Affiliations

¹ †Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, People's Republic of China.
² §Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, People's Republic of China.
³ ‡State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China.
⁴ ∥Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China.

PMID: 26090551
DOI: 10.1021/acs.orglett.5b01479

Abstract

2-Perfluoroalkylated indoles were efficiently synthesized via a one-pot cascade Michael-type addition/palladium-catalyzed intramolecular cross-dehydrogenative coupling (CDC) process, using molecular oxygen as the sole oxidant at 100 °C in DMSO. This process allows atom economical assembly of indole rings from inexpensive and readily available anilines and methyl perfluoroalk-2-ynoates and tolerates a broad range of functional groups.

Publication types

Research Support, Non-U.S. Gov't