Photocatalyzed intermolecular amination for the synthesis of hydrazonamides

Abstract

Hydrazonamides are fundamental building blocks in many pharmaceuticals and agricultural chemicals. Although contributions have been accomplished through multi-step reactions under harsh conditions, achieving high efficient synthetic strategy remains challenging. Considering...

Photocatalytic cross-dehydrogenative coupling reaction toward the synthesis of N,N-disubstituted hydrazides and their bromides

“…38 Our group also successfully developed a photocatalytic cross-dehydrogenative coupling of indoles and thiophenols using rose bengal as the photocatalyst at room temperature. 39 Inspired by previous reports, 40 we speculate that N,N-disubstituted hydrazides may be constructed by a CDC strategy from available materials under visible light irradiation through direct C(vO)-N-N bond formation. Herein we report a straightforward synthesis of N,N-disubstituted hydrazides and their bromides through a formal photocatalytic CDC of N,N-disubstituted hydrazines and aldehydes in one-pot under mild reaction conditions (Scheme 1f ).…”

“…N , N -Disubstituted hydrazines were prepared according to our previous reports. 40 The other starting materials, reagents and solvents were purchased commercially. Unless otherwise noted, all purchased products were used without further purification.…”

Radical coupling reactions of hydrazinesviaphotochemical and electrochemical strategies

“…After that, the same group reported developed an efficient photocatalytic cross-dehydrogenative coupling (CDC) method for the synthesis of N,N -disubstituted acyl hydrazides and their bromides from aldehydes and N,N -disubstituted hydrazines (Schemes 33 and 34). 36 Both aromatic and aliphatic aldehydes were compatible with this transformation. In addition, a variety of functional groups could be tolerated in the reaction, such as hydroxy, cyano, ester, trifluoromethyl and halogen groups, etc .…”

Copper-Catalyzed Phosphorylation of N,N-Disubstituted Hydrazines: Synthesis of Multisubstituted Phosphorylhydrazides as Potential Anticancer Agents

“…21 We also reported a photocatalyzed intermolecular coupling of N,N-disubstituted hydrazines with β-ketonitriles to hydrazonamides. 22 Additionally, cross-dehydrogenative coupling (CDC) reaction has been widely used as one of the most efficient synthetic strategies for the construction of various new C−X (X = C, N,O, S, P) bonds in recent decades. 23 In this context, we further developed an efficient copper-catalyzed aerobic oxidative cross-dehydrogenative coupling reaction for the synthesis of multisubstituted phosphorylhydrazides from N,N-disubstituted hydrazines and hydrogen phosphoryl compounds (Scheme 1e).…”

“…Organic hydrazines are a class of highly versatile and easily accessible coupling partners in organic synthesis . We also reported a photocatalyzed intermolecular coupling of N , N -disubstituted hydrazines with β-ketonitriles to hydrazonamides . Additionally, cross-dehydrogenative coupling (CDC) reaction has been widely used as one of the most efficient synthetic strategies for the construction of various new C–X (X = C, N,O, S, P) bonds in recent decades .…”