4.8 Article

Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 34, 页码 10958-10961

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AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b07842

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资金

  1. European Union for Beatriu de Pinos fellowhip
  2. EPSRC [EP/I038071/1]
  3. Bristol University
  4. EPSRC [EP/K03927X/1, EP/I038071/1, EP/K035746/1] Funding Source: UKRI
  5. Engineering and Physical Sciences Research Council [EP/K03927X/1, EP/I038071/1, EP/K035746/1] Funding Source: researchfish

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A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.

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