A metal-free photocatalytic Ritter-type C-H amination of unactivated sp carbons using molecular oxygen as a terminal oxidant has been developed. By employing a co-catalytic system of 3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) and -butyl nitrite (TBN), this novel strategy provides a low cost, sustainable and scalable way to synthesise a broad range of secondary amides in moderate to excellent yields under mild conditions.
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http://dx.doi.org/10.1039/d2ob01713j | DOI Listing |
Chem Commun (Camb)
July 2024
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.
Visible light-induced, transition metal-free oxidative dehydroxylation and C-H amidation of α-hydroxy ketones involving Ritter-type amidation has been developed, leading to the selective synthesis of α,α-diamido- and α-monoamido ketones with tunable selectivity as well as broad substrate tolerance.
View Article and Find Full Text PDFJ Org Chem
July 2023
College of Chemistry, Sichuan University, Wangjiang Road 29, Chengdu, Sichuan 610064, China.
A straightforward strategy for direct benzylic C-H bond amination an electrochemical Ritter-type reaction is developed. The reaction demonstrates simpler and milder reaction conditions over the existing methods without extra mediator. Moderate to excellent yields up to 94% of the desired amide products were obtained with a broad substrate scope.
View Article and Find Full Text PDFOrg Biomol Chem
November 2022
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China.
A metal-free photocatalytic Ritter-type C-H amination of unactivated sp carbons using molecular oxygen as a terminal oxidant has been developed. By employing a co-catalytic system of 3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) and -butyl nitrite (TBN), this novel strategy provides a low cost, sustainable and scalable way to synthesise a broad range of secondary amides in moderate to excellent yields under mild conditions.
View Article and Find Full Text PDFOrg Lett
April 2022
Department of Chemistry, Indian Institute of Technology Ropar, Lab no. 406, S. S. Bhatnagar Block, Rupnagar, Punjab 140001, India.
The synthesis of paracetamol still relies on multistep protocols involving the utilization of a stoichiometric amount of oxidizing/reducing or other corrosive agents. Herein we report a regioselective electrochemical Ritter-type reaction at the C(sp)-H of unprotected phenol toward the environmentally benign and direct synthesis of paracetamol. The reaction proceeds under exogenous oxidant- and catalyst-free conditions.
View Article and Find Full Text PDFJ Am Chem Soc
June 2021
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
A method for C-H bond amination via an electrophotocatalytic Ritter-type reaction is described. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion in an electrochemical cell under irradiation. These conditions convert benzylic C-H bonds to acetamides without the use of a stoichiometric chemical oxidant.
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