Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes

Version 1 : Received: 27 May 2021 / Approved: 31 May 2021 / Online: 31 May 2021 (09:14:12 CEST)

A peer-reviewed article of this Preprint also exists.

Lessi, M.; Nania, A.; Pittari, M.; Lodone, L.; Cuzzola, A.; Bellina, F. Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes. Catalysts 2021, 11, 762. Lessi, M.; Nania, A.; Pittari, M.; Lodone, L.; Cuzzola, A.; Bellina, F. Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes. Catalysts 2021, 11, 762.

Abstract

The construction of carbon-carbon bonds by direct involvement of two unactivated carbon-hydrogen bonds, without any directing group, ensures an high atom economy of the entire process. Here it is described a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CDC) of 5-arylimidazoles, benzimidazoles, benzoxazole and 4,5-diphenylimidazole at their C-2 position with functionalized styrenes. This specific CDC, known as Fujiwara-Moritani reaction or oxidative Heck coupling, allowed also the C-4 alkenylation of the imidazole nucleus when both 2 and 5 positions are occupied.

Keywords

C-H activation; imidazoles; Fujiwara-Moritani reaction; dehydrogenative coupling; oxidative Heck coupling; styrenes; palladium catalysis; copper salts

Subject

Chemistry and Materials Science, Analytical Chemistry

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