A Copper‐ and Phosphine‐Free Nickel(II)‐Catalyzed Method for C−H Bond Alkynylation of Benzothiazoles and Related Azoles | Zendy

Patel Ulhas N. | Zendy; Punji Benudhar | Zendy

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A Copper‐ and Phosphine‐Free Nickel(II)‐Catalyzed Method for C−H Bond Alkynylation of Benzothiazoles and Related Azoles

Author(s) -

Patel Ulhas N.,

Punji Benudhar

Publication year - 2018

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201800243

Subject(s) - chemistry , alkynylation , catalysis , phosphine , combinatorial chemistry , nickel , copper , homogeneous catalysis , medicinal chemistry , organic chemistry

A phosphine‐free nickel(II)‐catalyzed method for the C(2)−H bond alkynylation of (benzo)thiazoles, (benz)imidazoles, and oxazoles is described. Well‐defined and air‐stable (Phen)NiCl 2 catalyst efficiently catalyzes the coupling of diverse azoles with alkynyl bromides without the use of a copper co‐catalyst, and the method tolerates synthetically important functional groups. Preliminary mechanistic studies on this Ni II ‐catalyzed alkynylation emphasize the homogeneous nature of the catalyst, and rule out a radical manifold for the reaction. The synthetic utility of this Ni‐catalyzed method is demonstrated by further functionalizing the alkynylated benzothiazoles to 3‐methyl‐2‐(alkynyl)benzo[ d ]thiazolium salts that are known DNA cleaving agents.

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