4.5 Article

A General and Efficient Suzuki-Miyaura Cross-Coupling Protocol Using Weak Base and No Water: The Essential Role of Acetate

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 22, Pages 3688-3692

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900538

Keywords

Suzuki-Miyaura coupling; Cross-coupling; Boranes; Lewis bases; Palladium

Funding

  1. Natural Science Foundation of China [20832005]
  2. Youth Funding [20602008]
  3. Fudan University [EYH1615003]

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A weak base, CsOAc, promotes Suzuki-Miyaura cross-coupling and related Pd-catalyzed reactions under anhydrous conditions as effectively as stronger bases. Aryl triflates exhibit unusual reaction rates, which are comparable to that of bromoarenes. A neglected six-membered transition-state model was proposed to give alternative insight into the key process of transmetalation. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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