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

Yangyang Yang, Jet Tsien, Ayala Ben David, Jonathan M.E. Hughes, Rohan M. 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 other materials. 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 acid as a linchpin, 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 previously synthetically challenging high Fsp3-containing drug-like scaffolds.

Original languageEnglish (US)
JournalUnknown Journal
DOIs
StatePublished - Sep 29 2020

Keywords

  • Alkyl boron compounds
  • C(sp3)-rich
  • Modular coupling

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Science(all)

Fingerprint Dive into the research topics of 'A Practical and Modular Construction of C(sp<sup>3</sup>)-rich Alkyl Boron Compounds'. Together they form a unique fingerprint.

Cite this