Transition-Metal-Free Cross-Coupling by Using Tertiary Benzylic Organoboronates

  • Angew Chem Int Ed Engl. 2020 Dec 7;59(50):22460-22464. doi: 10.1002/anie.202010251.
Mitsutaka Takeda  1 ,  Kazunori Nagao  1 ,  Hirohisa Ohmiya  1  2
Affiliations
  • 1. Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
  • 2. JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan.
PMID: 32869918 DOI: 10.1002/anie.202010251
Abstract

The transition-metal-free cross-coupling of alkyl or aryl electrophiles by using tertiary benzylic organoboronates is reported. This reaction involves the generation of tertiary alkyl anions from organoboronates in the presence of an alkoxide base and then their substitution reactions. This protocol allows the simple and efficient construction of quaternary carbon centers.

Keywords
alkylation; cross-coupling; quaternary carbon centers; tertiary alkylboronates; transition-metal-free.
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