Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides

Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides

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...

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Bibliographic Details
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
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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