Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides

Xuan Wang, Guobin Ma, Yu Peng, Chloe E. Pitsch, Brenda J. Moll, Thu D. Ly, Xiaotai Wang*, Hegui Gong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

164 Citations (Scopus)

Abstract

This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation of cyclotryptamine derivatives, wherein successful incorporation of 7-indolyl moieties is of particular interest as numerous naturally occurring products are composed of these key scaffolds. DFT calculations have been carried out to investigate the proposed radical chain and double oxidative addition pathways, which provide useful mechanistic insights into the part of the reaction that takes place in solution.

Original languageEnglish
Pages (from-to)14490-14497
Number of pages8
JournalJournal of the American Chemical Society
Volume140
Issue number43
DOIs
Publication statusPublished - 31 Oct 2018
Externally publishedYes

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