Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed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

How to cite: 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. Preprints 2021, 2021050719 (doi: 10.20944/preprints202105.0719.v1). 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. Preprints 2021, 2021050719 (doi: 10.20944/preprints202105.0719.v1).

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.

Subject Areas

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

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