Literature DB >> 26839929

Brønsted acid-catalysed conjugate addition of photochemically generated α-amino radicals to alkenylpyridines.

Hamish B Hepburn1, Paolo Melchiorre.   

Abstract

The conjugate addition of α-amino radicals to alkenylpyridines has been accomplished by the synergistic merger of Brønsted acid and visible light photoredox catalysis. Key to reaction development was the protonation of the alkenylpyridines that transiently generated a highly reactive, electrophilic pseudo-iminium ion intermediate. Initial investigations using chiral phosphoric acids provide clues on the feasibility of an enantioselective catalytic variant.

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Year:  2016        PMID: 26839929     DOI: 10.1039/c5cc10401g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  8 in total

Review 1.  Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds.

Authors:  James E Gillespie; Alexander Fanourakis; Robert J Phipps
Journal:  J Am Chem Soc       Date:  2022-09-30       Impact factor: 16.383

2.  Cooperative Stereoinduction in Asymmetric Photocatalysis.

Authors:  Steven J Chapman; Wesley B Swords; Christine M Le; Ilia A Guzei; F Dean Toste; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2022-02-22       Impact factor: 16.383

3.  Highly enantioselective catalytic synthesis of chiral pyridines.

Authors:  Ravindra P Jumde; Francesco Lanza; Tilde Pellegrini; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2017-12-12       Impact factor: 14.919

4.  Reductive Hydroxymethylation of 4-Heteroarylpyridines.

Authors:  Hamish B Hepburn; Timothy J Donohoe
Journal:  Chemistry       Date:  2020-01-30       Impact factor: 5.236

5.  A Computational and Experimental Investigation of the Origin of Selectivity in the Chiral Phosphoric Acid Catalyzed Enantioselective Minisci Reaction.

Authors:  Kristaps Ermanis; Avene C Colgan; Rupert S J Proctor; Barbara W Hadrys; Robert J Phipps; Jonathan M Goodman
Journal:  J Am Chem Soc       Date:  2020-11-30       Impact factor: 15.419

6.  Asymmetric [3 + 2] photocycloadditions of cyclopropylamines with electron-rich and electron-neutral olefins.

Authors:  Yating Dai; Shuangshuang Liang; Guangkuo Zeng; Hongchun Huang; Xiaowei Zhao; Shanshan Cao; Zhiyong Jiang
Journal:  Chem Sci       Date:  2022-03-03       Impact factor: 9.825

7.  Radical-based functionalization-oriented construction: rapid assembly of azaarene-substituted highly functionalized pyrroles.

Authors:  Weigao Hu; Qiangqiang Zhan; Hongwei Zhou; Shanshan Cao; Zhiyong Jiang
Journal:  Chem Sci       Date:  2021-03-29       Impact factor: 9.825

8.  Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketones via N2H4 mediated deoxygenative couplings.

Authors:  Leiyang Lv; Chao-Jun Li
Journal:  Chem Sci       Date:  2020-12-30       Impact factor: 9.825

  8 in total

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