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author:

Shu, Xianli (Shu, Xianli.) [1] | Xu, Ruting (Xu, Ruting.) [2] | Liao, Saihu (Liao, Saihu.) [3]

Indexed by:

EI CSCD

Abstract:

Nitrogen-containing motifs are widely present in natural products, bioactive molecules, and drugs. Accordingly, effective synthetic methods with high efficiency and diversity are highly desirable. Here, we present the invention of a facile, visible light-mediated decarboxylative C(sp3)-N bond-forming reaction by employing abundant carboxylic acids as the feedstock and a commercial diazirine as a nitrogen donor. This process is amenable to access both imines and diaziridines, as the corresponding masked amines and hydrazines, through a selectable single or double nitrogen transfer from the diazirine, respectively. This divergent approach works well in both directions with various alkyl carboxylic acids, including primary, secondary, and tertiary acids, as well as natural products and drugs, thus affording a rapid, metal-free approach to build nitrogen-containing molecule libraries with considerable structural diversity, which could thus benefit the related study in context of chemical biology and drug discovery. [Figure not available: see fulltext.] © 2021, Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature.

Keyword:

Amines Carboxylic acids Drug products Hydrazine Molecules Nitrogen

Community:

  • [ 1 ] [Shu, Xianli]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 2 ] [Xu, Ruting]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 3 ] [Liao, Saihu]Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
  • [ 4 ] [Liao, Saihu]Beijing National Laboratory for Molecular Sciences, Beijing; 100190, China

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Source :

Science China Chemistry

ISSN: 1674-7291

Year: 2021

Issue: 10

Volume: 64

Page: 1756-1762

1 0 . 1 3 8

JCR@2021

1 0 . 4 0 0

JCR@2023

ESI HC Threshold:117

JCR Journal Grade:1

CAS Journal Grade:1

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 12

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 2

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