Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols

Org Lett. 2016 Apr 1;18(7):1590-3. doi: 10.1021/acs.orglett.6b00450. Epub 2016 Mar 23.

Abstract

An efficient palladium-catalyzed direct arylation of pyridylmethyl silyl ethers with aryl bromides is described. A Pd(OAc)2/NIXANTPHOS-based catalyst provides aryl(pyridyl)methyl alcohol derivatives in good to excellent yields (33 examples, 57-100% yield). This protocol is compatible with different silyl ether protecting groups, affording either the protected or the free alcohols in an effective one-pot process. The scalability of the reaction is demonstrated.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzyl Compounds / chemistry*
  • Catalysis
  • Ethers / chemistry*
  • Methanol / analogs & derivatives
  • Methanol / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry

Substances

  • Benzyl Compounds
  • Ethers
  • Pyridines
  • Palladium
  • Methanol