Asymmetric oxidative Mannich reactions promoted by photocatalysis and electrochemistry

Abstract

The asymmetric Mannich reaction is an essential method in contemporary organic chemistry. As the representative of clean and green synthesis methods, photochemical and electrochemical oxidation strategies have re-emerged in recent...

Direct Reductive Arylation of Imines with Electron-Deficient (Hetero) Arenes via Electrosynthesis to Access Benzylic Amines

“…Considerable progress has been made in the use of aryl radicals for arylation over the past few decades; however, a key limitation in using aryl radicals is related to the difficulty of their generation. As chemists explore more efficient ways to advance chemistry, electrosynthesis has received increasing attention because it can not only replace traditional oxidizing or reducing agents with sustainable electricity, which is in line with green chemistry, but also can be used as a mild technique to provide a much broader scope of reactivity . The recently successfully developed radical arylation has benefited largely from the progress of current-induced organic reactions.…”

Electricity-driven asymmetric bromocyclization enabled by chiral phosphate anion phase-transfer catalysis

“…In the past few decades, substantial efforts have been devoted to asymmetric electrosynthesis. Impressive progress has been achieved by the strategic introduction of different chiral factors, including chiral electrode surface, chiral solvent, chiral electrolyte, chiral auxiliary, chiral mediator, and chiral catalyst [17][18][19][20][21][22][23][24][25] . Among these strategies, the use of a chiral catalyst for asymmetric amplification represents the most attractive approach [19][20][21][22][23][24][25] .…”

“…Impressive progress has been achieved by the strategic introduction of different chiral factors, including chiral electrode surface, chiral solvent, chiral electrolyte, chiral auxiliary, chiral mediator, and chiral catalyst [17][18][19][20][21][22][23][24][25] . Among these strategies, the use of a chiral catalyst for asymmetric amplification represents the most attractive approach [19][20][21][22][23][24][25] . However, it is not straightforward to implement asymmetric catalysis in an electrochemical context.…”

“…Various compatibility issues need to be addressed in order to achieve both high efficiency and excellent asymmetric induction. Although a number of efficient electrocatalytic asymmetric transformations have been developed in the past decade, the modes of asymmetric induction are rather limited and there remain unsolved questions [19][20][21][22][23][24][25] .…”

“…1a) 15,16 . However, their applicability in electrochemistry varied significantly [19][20][21][22][23][24][25] . Among them, covalent bonding with a chiral catalyst proved most successful [26][27][28][29][30][31][32] .…”