Making C-N and C-P bonds on the quinone derivatives through the assistance of silver-mediated C-H functionalization processes

Recent Advances in Direct Functionalization of Quinones

“…Silver salts played a versatile role in this reaction, as a mediator for facilitating the consecutive additions of Ar 2 P(=O) and aniline to the related carbon atoms of 1,4‐benzoquinone, as an oxidant of hydroquinone intermediates to form the substituted 1,4‐benzoquinone counterpart. In the same year, a related work on C–N and C–P bond formation of quinones was achieved by the same group . The proposed mechanism from the authors was shown in Scheme .…”

The Different Facets of Metal‐Catalyzed C−H Functionalization Involving Quinone Compounds

“…An interesting Ag‐mediated phosphination/amination reaction of quinones was reported by Hong and co‐workers in 2017 (Scheme 62). [98,99] During an attempted phosphination of diphenylmethanimine using Ag(I), Pd(OAc) 2 and benzoquinone as a co‐catalyst, the diarylphosphine oxide and aniline adduct of benzoquinone was instead isolated. After extensive probing of the reaction conditions, some conclusions were made regarding the mechanism of this transformation.…”

Theoretical studies to predict the utility of diazo esters in their reactions with 1,4-quinones: experimental validation via a visible light driven metal free process

“…19–27 The importance of 1,4-quinones has prompted a plethora of methods for the direct functionalization of quinones. 28–69 The different processes that are available include: (i) oxidative radical coupling for alkylations and arylations; (ii) photoinduced radical coupling and synergistic addition/oxidative reactions for alkylations; (iii) transition metal catalysed oxidative Heck type coupling reactions; and (iv) metal catalysed amination, phosphination and sulfenylation. 28–64 Recently, blue LED induced protocols for the functionalization of 1,4-quinones have also been reported.…”

“…28–69 The different processes that are available include: (i) oxidative radical coupling for alkylations and arylations; (ii) photoinduced radical coupling and synergistic addition/oxidative reactions for alkylations; (iii) transition metal catalysed oxidative Heck type coupling reactions; and (iv) metal catalysed amination, phosphination and sulfenylation. 28–64 Recently, blue LED induced protocols for the functionalization of 1,4-quinones have also been reported. 65–69 The notable ones are Rao et al 's base mediated cascade reaction involving perfluoroalkyl iodides, alkenes and arylamino-1,4-naphthoquinones under blue LEDs and Jin and co-workers’ blue LED induced reactions of electron donor–acceptor complexes involving tandem cyclization and subsequent arylation of unactivated alkenes with 2-amino-1,4-naphthoquinones.…”