Literature DB >> 30829425

Photoinduced C(sp3 )-N Bond Cleavage Leading to the Stereoselective Syntheses of Alkenes.

Ze-Kun Yang1,2, Ning-Xin Xu1, Chao Wang1,2, Masanobu Uchiyama1,2.   

Abstract

Herein we report a versatile Mizoroki-Heck-type photoinduced C(sp3 )-N bond cleavage reaction. Under visible-light irradiation (455 nm, blue LEDs) at room temperature, alkyl Katritzky salts react smoothly with alkenes in a 1:1 molar ratio in the presence of 1.0 mol % of commercially available photoredox catalyst without the need for any base, affording the corresponding alkyl-substituted alkenes in good yields with broad functional-group compatibility. Notably, the E/Z-selectivity of the alkene products can be controlled by an appropriate choice of photoredox catalyst.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−N bond cleavage; Mizoroki-Heck reaction; alkenes; amines; photoredox catalysis

Year:  2019        PMID: 30829425     DOI: 10.1002/chem.201900886

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 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.  Beyond Retigabine: Design, Synthesis, and Pharmacological Characterization of a Potent and Chemically Stable Neuronal Kv7 Channel Activator with Anticonvulsant Activity.

Authors:  Simona Musella; Lidia Carotenuto; Nunzio Iraci; Giulia Baroli; Tania Ciaglia; Piera Nappi; Manuela Giovanna Basilicata; Emanuela Salviati; Vincenzo Barrese; Vincenzo Vestuto; Giuseppe Pignataro; Giacomo Pepe; Eduardo Sommella; Veronica Di Sarno; Michele Manfra; Pietro Campiglia; Isabel Gomez-Monterrey; Alessia Bertamino; Maurizio Taglialatela; Carmine Ostacolo; Francesco Miceli
Journal:  J Med Chem       Date:  2022-08-16       Impact factor: 8.039

6.  Deaminative Reductive Methylation of Alkylpyridinium Salts.

Authors:  Olivia P Bercher; Shane Plunkett; Thomas E Mortimer; Mary P Watson
Journal:  Org Lett       Date:  2021-08-31       Impact factor: 6.072

7.  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

8.  Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.

Authors:  Soniya Rani; Soumya Ranjan Dash; Asish Bera; Md Nirshad Alam; Kumar Vanka; Pradip Maity
Journal:  Chem Sci       Date:  2021-05-28       Impact factor: 9.825

  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.