ABSTRACT
Correction for 'Radical alkylation of isocyanides with amino acid-/peptide-derived Katritzky salts via photoredox catalysis' by Ze-Fan Zhu, et al., Org. Biomol. Chem., 2019, 17, 1531-1534.
ABSTRACT
An efficient and mild method was developed for the synthesis of 6-alkylated phenanthridines upon visible light irradiation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amino acids/peptides were used as radical precursors for the alkylation of isocyanobiphenyl species. The reaction displays an excellent functional group tolerance and a potential utility for peptide functionalization, allowing access to desired products in good to excellent yields.
Subject(s)
Amino Acids/chemistry , Cyanides/chemistry , Peptides/chemistry , Photochemical Processes , Salts/chemistry , Alkylation , Catalysis , Oxidation-ReductionABSTRACT
The use of aliphatic amines as alkylating reagents in organic synthesis via C-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis of meta-alkylated arenes via dual C-H and C-N activation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amines and amino acid species were used as alkyl radical precursors. This catalytic reaction could accommodate a broad range of functional groups and provide access to various meta-alkylated products.
ABSTRACT
A regioselective cis-hydroalkylation of internal alkynes with readily prepared Katritzky pyridinium salts for the synthesis of tri-substituted alkenes is described. This reaction is the first example of a metal-catalyzed hydroalkylation of an alkyne via C-N bond activation of an amine. The reaction demonstrates broad scope and functional group tolerance, allowing access to desired products with high diversity. Preliminary mechanistic studies indicate that a combination of an SET-initiated radical process and Ni-catalyzed alkylation could engage in the reaction, which makes it possible to bypass the traditional open-shell addition pathway.
ABSTRACT
An efficient and mild oxycyanation of vinyl ethers with 2,2,6,6-tetramethyl-N-oxopiperidinium and TMSCN is described. The mechanistic studies indicated that the formation of an electron donor-acceptor complex and subsequent single-electron-transfer process could be involved in the reaction.