My groups recently developed new procedures for modification of unsaturated heterocycles, by using palladium catalysts. We employed palladium radical catalysis to generate alkyl radicals. The nucleophilic radicals then added efficiently to major families of heteroarenes with substrate generality. In the second example, we achieved arylation of azoles and thiophenes, which also introduced ortho-alkyl groups on aryl halides at the same time, under Catellani-type conditions. In the last example, we realized C-C cross-coupling of cyclopropyl halides with both azoles and thiophenes. The reaction was stereo-retentive on the three-membered rings.

Alkylation, arylation, and cyclopropylation of common heterocycles via palladium catalysis

253rd National Meeting (2017)

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