Literature DB >> 30681112

Radical alkylation of isocyanides with amino acid-/peptide-derived Katritzky salts via photoredox catalysis.

Ze-Fan Zhu1, Miao-Miao Zhang, Feng Liu.   

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.

Entities:  

Mesh:

Substances:

Year:  2019        PMID: 30681112     DOI: 10.1039/c8ob02786b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  9 in total

1.  Engaging Alkenes and Alkynes in Deaminative Alkyl-Alkyl and Alkyl-Vinyl Cross-Couplings of Alkylpyridinium Salts.

Authors:  Kristen M Baker; Diana Lucas Baca; Shane Plunkett; Mitchell E Daneker; Mary P Watson
Journal:  Org Lett       Date:  2019-11-25       Impact factor: 6.005

2.  Deaminative Arylation of Amino Acid-derived Pyridinium Salts.

Authors:  Megan E Hoerrner; Kristen M Baker; Corey H Basch; Earl M Bampo; Mary P Watson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

Review 3.  Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

Authors:  Yuan Gao; Songwei Jiang; Nian-Dong Mao; Huan Xiang; Ji-Long Duan; Xiang-Yang Ye; Li-Wei Wang; Yang Ye; Tian Xie
Journal:  Top Curr Chem (Cham)       Date:  2022-05-19

4.  Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines.

Authors:  Julia R Dorsheimer; Melissa A Ashley; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-11-12       Impact factor: 15.419

5.  Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.

Authors:  Sergei Tcyrulnikov; Qiuqi Cai; J Cameron Twitty; Jianyu Xu; Abderrahman Atifi; Olivia P Bercher; Glenn P A Yap; Joel Rosenthal; Mary P Watson; Marisa C Kozlowski
Journal:  ACS Catal       Date:  2021-06-28       Impact factor: 13.700

Review 6.  Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review.

Authors:  Alessandra Del Tito; Havall Othman Abdulla; Davide Ravelli; Stefano Protti; Maurizio Fagnoni
Journal:  Beilstein J Org Chem       Date:  2020-06-25       Impact factor: 2.883

Review 7.  New avenues for C-B bond formation via radical intermediates.

Authors:  Florian W Friese; Armido Studer
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

8.  Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization.

Authors:  Carlo Sambiagio; Matteo Ferrari; Koen van Beurden; Nicola Della Ca'; Jack van Schijndel; Timothy Noël
Journal:  Org Lett       Date:  2021-03-02       Impact factor: 6.005

9.  Solid-Phase Peptide Modification via Deaminative Photochemical Csp3 -Csp3 Bond Formation Using Katritzky Salts.

Authors:  Joseph Openy; Gulshan Amrahova; Jen-Yao Chang; Anaïs Noisier; Peter 't Hart
Journal:  Chemistry       Date:  2022-05-26       Impact factor: 5.020

  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.