Palladium-Catalyzed Direct Arylation of Polyfluoroarenes for Accessing Tetra- ortho-Substituted Biaryls: Buchwald-type Ligand Having Complementary -PPh2 Moiety Exhibits Better Efficiency

On Ying Yuen, Man Pan Leung, Chau Ming So, Raymond Wai Yin Sun, Fuk Yee Kwong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

7 Citations (Scopus)

Abstract

The first general examples of direct C-H arylation of electron-deficient polyfluoroarenes with challenging di-ortho-substituted aryl(heteroaryl) chlorides for tetra-ortho-substituted biaryl synthesis are reported. Key to success is the use of Buchwald-type biaryl phosphine ligand, notably with inexpensive -PPh2 moiety (instead of -PCy2 group). Pd(OAc)2 associated with ligand L9 exhibits even higher efficiency than the corresponding SPhos toward this reaction. A wide range of sterically hindered di-ortho-substituted chloroarenes bearing electron-donating or -withdrawing groups are found applicable. Excellent product yields are obtained under mild reaction conditions, and the catalyst loading down to 0.25 mol % of Pd can also be achieved.

Original languageEnglish
Pages (from-to)9008-9017
Number of pages10
JournalJournal of Organic Chemistry
Volume83
Issue number16
DOIs
Publication statusPublished - 17 Aug 2018

ASJC Scopus subject areas

  • Organic Chemistry

Cite this