Literature DB >> 30974006

Visible-Light-Mediated Charge Transfer Enables C-C Bond Formation with Traceless Acceptor Groups.

Michael J James1, Felix Strieth-Kalthoff1, Frederik Sandfort1, Felix J R Klauck1, Felicitas Wagener1, Frank Glorius1.   

Abstract

The development and application of traceless acceptor groups in photochemical C-C bond formation is described. This strategy was enabled by the photoexcitation of electron donor-acceptor (EDA) complexes with visible light. The traceless acceptors, which were readily prepared from amino acid and peptide feedstocks, could be used to alkylate a wide range of heteroarene and enamine donors under metal- and peroxide-free conditions. The crucial role of the EDA complexes in the mechanism of these reactions was explored through combined experimental and computational studies.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond formation; amino acids; donor-acceptor systems; traceless acceptors; visible light

Year:  2019        PMID: 30974006     DOI: 10.1002/chem.201901397

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


  18 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

Review 4.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

5.  Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.

Authors:  Bill J Motsch; Sarah E Wengryniuk
Journal:  Org Lett       Date:  2022-08-08       Impact factor: 6.072

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.  α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines.

Authors:  Kristen M Baker; Amanda Tallon; Richard P Loach; Olivia P Bercher; Matthew A Perry; Mary P Watson
Journal:  Org Lett       Date:  2021-09-27       Impact factor: 6.072

8.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

9.  Divergent reactivity of sulfinates with pyridinium salts based on one- versus two-electron pathways.

Authors:  Myojeong Kim; Euna You; Seongjin Park; Sungwoo Hong
Journal:  Chem Sci       Date:  2021-03-31       Impact factor: 9.825

10.  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

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