Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: efficient access to α-alkyl vinylarenes

Chem Commun (Camb). 2015 Aug 18;51(64):12771-4. doi: 10.1039/c5cc05312a.

Abstract

Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA)2/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 °C under 1 atm of O2 without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Electrons*
  • Hydrocarbons, Aromatic / chemistry*
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Hydrocarbons, Aromatic
  • Palladium
  • Oxygen