A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides

On Ying Yuen, Chau Ming So, Ho Wing Man, Fuk Yee Kwong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

22 Citations (Scopus)

Abstract

KGaA, Weinheim. A general palladium-catalyzed Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryl and heteroaryl trialkoxysilanes by a Pd(OAc)2/L2 catalytic system is presented. A newly developed water addition protocol can dramatically improve the product yields. The conjugation of the Pd/L2 system and the water addition protocol can efficiently catalyze a broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl chlorides and heteroaryl chlorides with excellent yields within three hours and the catalyst loading can be down to 0.05 mol % Pd for the first time. Hiyama coupling of heteroaryl chlorides with heteroaryl silanes is also reported for the first time. The reaction can be easily scaled up 200 times (100 mmol) without any degasification and purification of reactants; this facilitates the practical application in routine synthesis.
Original languageEnglish
Pages (from-to)6471-6476
Number of pages6
JournalChemistry - A European Journal
Volume22
Issue number19
DOIs
Publication statusPublished - 4 May 2016

Keywords

  • aryl chlorides
  • aryl(alkoxy)silane
  • cross-coupling reaction
  • palladium
  • phosphine ligand

ASJC Scopus subject areas

  • Chemistry(all)

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