A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF, has been developed for the photodeprotection of benzenesulfonyl-protected -heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the -heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.0c00983 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Developing efficient and novel methodologies to construct a C-C bond is highly important in both synthetic chemistry and pharmaceutical sciences. In recent years, the visible light-mediated desulfonylative transformation of sulfonyl compounds has emerged as a powerful tool for the synthesis of diverse C-C bond. To emphasize their practical utility, many methodologies have been successfully applied in the modification of a variety of biologically active compounds which possess unprotected amide or hydroxy groups.
View Article and Find Full Text PDFTransition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor.
J Org Chem
November 2020
INFIQC, Facultad de Ciencias Quı́micas, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina.
Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of -sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of -methyl--arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction.
View Article and Find Full Text PDFA visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses.
Chem Commun (Camb)
September 2020
Institute of Chemical and Engineering Sciences (ICES) Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros, #07-01, 138665, Singapore.
A decarboxylative, desulfonylative Smiles rearrangement is presented that employs activated-ester/energy transfer catalysis to decarboxylate β-amino acid derived starting materials at room-temperature under visible light irradiation. The radical Smiles rearrangement gives a range of biologically active arylethylamine products highly relevant to the pharmaceutical industry, chemical biology and materials science. The reaction is then applied to the synthesis of a chiral unnatural amino acid, 2-thienylalanine, used in the treatment of phenylketonuria.
View Article and Find Full Text PDFVisible-Light-Mediated -Desulfonylation of -Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst.
J Org Chem
July 2020
Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, Massachusetts 02210, United States.
A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF, has been developed for the photodeprotection of benzenesulfonyl-protected -heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the -heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!