Synthesis of Heteroaryl Compounds through Cross-Coupling Reaction of Aryl Bromides or Benzyl Halides with Thienyl and Pyridyl Aluminum Reagents

Abstract

An efficient method for synthesis of useful biaryl building blocks containing 2-thienyl, 3-thienyl, 2-pyridyl, and 3-pyridyl moieties was provided through cross-coupling reactions of aryl bromides or benzyl halides with heteroaryl aluminum reagents in the presence of Pd­(OAc)₂ and (<i>o</i>-tolyl)₃P. The coupling reaction also worked efficiently with heteroaryl bromides affording series of heterobiaryl compounds. The reaction of phenylbromide with in situ prepared 3-pyridyl aluminum was demonstrated to afford the product <b>8a</b> in high yield. Additionally, the catalytic system was also suited well for the coupling reaction of benzyl halides with pyridyl aluminum reagents to afford series of pyridyl-arylmethane