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Palladium-Catalyzed Double CH Activation Directed by Sulfoxides in the Synthesis of Dibenzothiophenes

✍ Scribed by Dr. Rajarshi Samanta; Dr. Andrey P. Antonchick


Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
308 KB
Volume
50
Category
Article
ISSN
0044-8249

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✦ Synopsis


C Γ€ H functionalization is a sustainable and straightforward approach to complex substances. [1] Numerous practical methods for the formation of CΓ€C, CΓ€N, and CΓ€O bonds through direct CΓ€H activation have been developed using transitionmetal catalysis. The activation of C(sp 2 )Γ€H bonds of aromatic compounds provides access to key scaffolds of natural products, drugs, and materials. Double C Γ€ H activation is a challenging, attractive, and highly economical method to create CΓ€C biaryl bonds. [2,3] However, the previously developed methods often suffer from selectivity problems in the formation of substituted biaryls and require a great excess of one coupling partner. For the efficient solution to this problem a number of directing groups such as carbonylbased or nitrogen-containing groups have been used. The development of efficient methods for the construction of complex molecules by multiple CΓ€H functionalization poses a great challenge. Herein, we report our preliminary results on a palladium-catalyzed double CΓ€H activation using sulfoxide as a new traceless directing group, and its application in a highly regioselective synthesis of polysubstituted dibenzothiophenes through a cascade reaction (Scheme 1).


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