Palladium-catalyzed distal selective C–H chalcogenation of biphenyl amines

Abstract

A palladium-catalyzed distal C(sp2)–H chalcogenation of biphenyl amines is described. This protocol demonstrates scalable, excellent chemo- and regio-selectivity, as well as broad functional groups tolerance, provides an efficient access to...

Visible-light-driven PCy3-promoted deselenization of 1,2-diselenides

“…Diaryl diselenides bearing various substituents including methyl (36 and 40), halogen (37-39), and trifluoromethyl (41) were accommodated under the reaction conditions. These deselenizative cross couplings were also operable with various derivatives of dibenzyl diselenide (42)(43)(44)(45)(46)(47). Efficient deselenizative cross-couplings were achieved with other diselenides such as diallyl diselenides and diacyl diselenides, affording the corresponding unsymmetrical monoselenides in good yields (48)(49)(50)(51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64).…”

“…[34][35][36][37][38][39][40] On the one hand, diselenides are more readily available than monoselenides. [41][42][43][44][45][46][47][48][49] On the other hand, most of the established methods for the synthesis of monoselenides are more or less inevitably accompanied by the formation of diselenides that are difficult to remove from the mixture due to their similar polarity to monoselenides (Fig. 2C).…”

“…Moreover, the unique electronic properties of selenium make this element indispensable in organic materials such as high-performance organic semiconductors for field-effect transistors 13–16 and thin film transistors. 17 Therefore, the development of an efficient method 18–20,41–61 for the construction of the C–Se bond has received continuous attention recently in organochalcogenide chemistry.…”

Rh(III)-Catalyzed Atroposelective C–H Selenylation of 1-Aryl Isoquinolines

“…Although traditional approaches have been well-developed to prepare organoselenides, it remains a great challenge to directly construct a C–Se bond through transition-metal-catalyzed direct C–H bond functionalization, probably because of the strong coordination between organoselenide and metal . Nevertheless, transition-metal-catalyzed C–H selenylations have been realized with the assistance of various directing groups over the past decade. − In 2014, Nishihara and co-workers pioneered Pd­(II)-catalyzed C–H selenylation of benzamides, benzylamines, and 2-arylpyridines with diselenides . In 2015, Li and co-workers reported the first example of Rh­(III)-catalyzed C–H selenylation of arenes bearing oxime, azo, pyridyl, or N -oxide chelating group with selenenyl chlorides or diselenides .…”