Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides

• Main Authors: Lei, Chuanhu, Jin, Xiaojia, Zhou, Jianrong (Steve)
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2016
• Subjects: alkynylation; CH activation; Catellani reaction; benzofuran; palladium catalysis
• Online Access: https://hdl.handle.net/10356/80269; http://hdl.handle.net/10220/40513
• Institution: Nanyang Technological University

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.