4.8 Article

Nickel-Catalyzed Cross-Couplings of Benzylic Pivalates with Arylboroxines: Stereospecific Formation of Diarylalkanes and Triarylmethanes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 9, Pages 3307-3310

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja312087x

Keywords

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Funding

  1. NSF [CHE 1151364]
  2. National Institute of General Medical Sciences of the NIH [P20GM103541]
  3. NIH [NSF MIR 0421224, NIH P20 RR017716]
  4. Division Of Chemistry
  5. Direct For Mathematical & Physical Scien [1151364, 1229234] Funding Source: National Science Foundation

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We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)(2) as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

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