Practical and Modular Construction of C(sp3)-Rich Alkyl Boron Compounds

Yangyang Yang, Jet Tsien, Ayala Ben David, Jonathan M.E. Hughes, Rohan R. Merchant, Tian Qin

Research output: Contribution to journalArticlepeer-review

Abstract

Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method is extensively examined through a variety of substrates, including synthesis and late-stage functionalization of scaffolds relevant to medicinal chemistry. The strategic significance of this approach, with alkyl boronic acids as linchpins, is demonstrated through various downstream functionalizations of the alkyl boron compounds. This two-step concurrent cross-coupling approach, resembling formal and flexible alkyl-alkyl couplings, provides a general entry to synthetically challenging high Fsp3-containing drug-like scaffolds.

Original languageEnglish (US)
Pages (from-to)471-480
Number of pages10
JournalJournal of the American Chemical Society
Volume143
Issue number1
DOIs
StatePublished - Jan 13 2021

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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