4.8 Article

Photocatalyst- and additive-free site-specific C(sp3)-H hydrazination of glycine derivatives and peptides

期刊

GREEN CHEMISTRY
卷 23, 期 14, 页码 5082-5087

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc01210j

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资金

  1. National Key R&D Program of China [2018YFB1501600]
  2. National Natural Science Foundation of China [21901237, 51821006, 51961135104]
  3. Anhui Provincial Natural Science Foundation [1908085QB53]

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A visible light-mediated protocol for site-specific C(sp(3))-H hydrazination of glycine derivatives and peptides with azo compounds has been developed. This reaction proceeds smoothly under photo-irradiation conditions in the absence of any catalysts and additives, providing a convenient method for efficient preparation of unnatural alpha-amino acids and precise modification of short peptides. Mechanism investigations suggest that single electron transfer (SET) and hydrogen atom transfer (HAT) may occur during this transformation.
A visible light-mediated protocol for site-specific C(sp(3))-H hydrazination of glycine derivatives and peptides with azo compounds has been developed. This C(sp(3))-N coupling reaction proceeded smoothly under photo-irradiation conditions in the absence of any catalysts and additives, thus providing a convenient and facile method for efficient preparation of unnatural alpha-amino acids and precise modification of short peptides. Mechanism investigations revealed that single electron transfer (SET) and hydrogen atom transfer (HAT) may occur during this transformation.

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