Visible‐Light‐Promoted C(sp<sup>3</sup>)−H Alkylation by Intermolecular Charge Transfer: Preparation of Unnatural α‐Amino Acids and Late‐Stage Modification of Peptides

Wang, Chao; Qi, Rupeng; Xue, Hongxiang; Shen, Yuxuan; Chang, Min; Chen, Yaqiong; Wang, Rui; Xu, Zhaoqing

doi:10.1002/ange.201914555

Cited by 36 publications

(19 citation statements)

References 85 publications

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“…In 2020, Xu and colleagues [ 39 ] proposed a visible-light-promoted alkylation reaction using Katritzky salts such as 128 and glycine derivative 127 (or glycine segments in peptides) initiated by an EDA complex. This successfully realized the simple synthesis of unnatural α-amino acids 129 and precise alkylation modification of peptides in the later stage ( Scheme 45 ).…”

Section: Reviewmentioning

confidence: 99%

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

Yang¹,

Liu²,

Cao³

et al. 2021

Beilstein J. Org. Chem.

130

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The reversible, weak ground-state aggregate formed by dipole–dipole interactions between an electron donor and an electron acceptor is referred to as an electron-donor–acceptor (EDA) complex. Generally, upon light irradiation, the EDA complex turns into the excited state, causing an electron transfer to give radicals and to initiate subsequent reactions. Besides light as an external energy source, reactions involving the participation of EDA complexes are mild, obviating transition metal catalysts or photosensitizers in the majority of cases and are in line with the theme of green chemistry. This review discusses the synthetic reactions concerned with EDA complexes as well as the mechanisms that have been shown over the past five years.

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Section: Reviewmentioning

confidence: 99%

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

Yang¹,

Liu²,

Cao³

et al. 2021

Beilstein J. Org. Chem.

130

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“…Very recently,X ua nd co-workers reported ar emarkable light-mediated, catalyst-free C À Ha lkylation of Gly using alkylpyridinium salts as alkyl radical precursors (Scheme 26). [73] Thekey step in the reaction is the formation of an electron-donor-acceptor (EDA) complex between Gly and the pyridinium salt, which upon irradiation undergoes an intermolecular charge transfer to generate an alkyl radicalafter homolytic cleavage of the NÀCb ond-and aG lyderived a-amino radical. These two species can undergo ar adical-radical coupling,t hereby allowing the straightforward derivatisation of Gly under very mild conditions.T his was highlighted by the selective derivatisation of Gly residues on several peptides.…”

Section: Glycine (Gly)mentioning

confidence: 99%

Radical‐Based Synthesis and Modification of Amino Acids

et al. 2020

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AdriµnG ómez-Suµrez graduated from the University of Santiago de Compostela in 2009. In 2014 he was awarded his PhD from the University of St. Andrews for his studies on the chemistry of dinuclear gold complexes under the supervision of Prof. Steven P. Nolan. Forp ostdoctoral research he moved to the WWU Münster to work with Prof. Frank Glorius. In 2018 he started his habilitation at the Bergische Universität Wuppertal, under the mentorship of Prof. Stefan F. Kirsch. His research interests include radical chemistry,c atalysis, and photochemistry. Scheme 1. Syntheses of a,b-diamino esters. Scheme 2. Synthesis of C-glyco-a-AAs.

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“…[72] Diese Tr ansformation erfolgt über die Koordinationsaktivierung eines 2-Picolinamido-a-aminoesters mit einer hochvalenten Ni III Erst kürzlich berichtete Xu über eine bemerkenswerte lichtvermittelte,k atalysatorfreie C-H-Alkylierung von Gly unter Verwendung von Alkylpyridiniumsalzen als Alkylradikalvorläufer (Abbildung 26). [73] Der Schlüsselschritt dieser Reaktion ist die Bildung eines Elektronen-Donor-Akzeptor-Komplexes (EDA-Komplex) zwischen Gly und dem Pyridiniumsalz. Bei Bestrahlung führt ein intermolekularer Ladungstransfer zur Bildung eines Alkylradikals -d urch homolytische Spaltung der N-C-Bindung -u nd eines vom Gly abgeleiteten a-Aminoradikals.D iese beiden Spezies kçnnen eine Radikal-Radikal-Kupplung eingehen, was die einfache Derivatisierung von Gly unter sehr milden Bedingungen ermçglicht.…”

Section: Glycin (Gly)unclassified