4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 50, Pages 22460-22464

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202010251

Keywords

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

Funding

  1. JSPS KAKENHI [JP18H01971, JP17H06449, JP20J20600]
  2. JST, PRESTO [JPMJPR19T2]

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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.

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