Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides
Zhou, Jianrong (Steve)
Date of Issue2016
School of Physical and Mathematical Sciences
We report an efficient alkynylation reaction of aryl iodides with simultaneous ortho-alkylaton of aryl rings. The reaction between three simple reagents—aryl halides, alkynes, and alkyl halides—formed aryl–alkynyl bonds carrying hindered aryl rings in one step. The reaction proceeded via a Catellani-type pathway in the presence of norbornene. From a synthetic perspective, this reaction allows quick access toward many 1,2,3-substituted arenes and multiply substituted benzofurans, after manipulation of alkyne groups. These compounds are difficult to synthesize otherwise.
© 2016 American Chemical Society.