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1.
Org Biomol Chem ; 17(14): 3640, 2019 04 03.
Article in English | MEDLINE | ID: mdl-30907902

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.

2.
Org Biomol Chem ; 17(6): 1531-1534, 2019 02 06.
Article in English | MEDLINE | ID: mdl-30681112

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-Reduction
3.
Chem Commun (Camb) ; 57(27): 3411-3414, 2021 Apr 07.
Article in English | MEDLINE | ID: mdl-33687414

ABSTRACT

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.

4.
Chem Commun (Camb) ; 55(76): 11478-11481, 2019 Sep 19.
Article in English | MEDLINE | ID: mdl-31490479

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.

5.
Org Lett ; 20(3): 720-723, 2018 02 02.
Article in English | MEDLINE | ID: mdl-29345943

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.

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