Intramolecular Csp<sup>3</sup>–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

Wen, Xiaojin; Li, Xinyao; Luo, Xiaoling; Wang, Weijin; Song, Song; Jiao, Ning

doi:10.1039/c9sc05522c

Cited by 16 publications

(10 citation statements)

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“…Jiao et al reported the synthesis of cyclic imines and tertiary amines through the intramolecular Csp 3 –H/C–C bond amination of alkylazide substrates 614 bearing a pendant aryl group ( Scheme 80 ) [ 175 ]. They found that in the presence of DDQ oxidant and TFA, the oxidation of substrates 614 could lead to the corresponding benzyl cation 616 , which could be attacked intramolecularly by the azide moiety.…”

Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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Section: Synthetic Methodology Involving C–h Functionalization Alomentioning

confidence: 99%

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Azizollahi

Garcı́a-López

2020

Molecules

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“…This allows for the formation of nitrogen-containing heterocycles, as shown in Scheme 32. 92 Oxidizing azide 158 with DDQ in the presence of trifluoroacetic acid (TFA) cleaves the benzylic C–H bond, leading to the azido group adding to form intermediate 159 . Hydride migration to nitrogen releases N 2 , and proton loss forms cyclic imine 160 .…”

Section: Quinone Oxidantsmentioning

confidence: 99%

Synthetic applications of hydride abstraction reactions by organic oxidants

et al. 2022

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“…Therefore, developing new and efficient approaches for the synthesis of α-ketotetrazoles is in urgent demand. 5…”

mentioning

confidence: 99%

The electrochemically enabled α-C(sp³)–H azolation of ketones

Fang,

Zhong,

Zeng

et al. 2023

Chem. Commun.

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Intramolecular Csp³–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

Abstract: A novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines has been developed. The aliphatic C–H or C–C bond was selectively cleaved with the efficient formation of two C–N single bonds or a CN double bond.

Cited by 16 publications

References 105 publications

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Synthetic applications of hydride abstraction reactions by organic oxidants

The electrochemically enabled α-C(sp³)–H azolation of ketones

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Intramolecular Csp3–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

Abstract: A novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines has been developed. The aliphatic C–H or C–C bond was selectively cleaved with the efficient formation of two C–N single bonds or a CN double bond.

Cited by 16 publications

References 105 publications

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Synthetic applications of hydride abstraction reactions by organic oxidants

The electrochemically enabled α-C(sp3)–H azolation of ketones

Contact Info

Product

Resources

About

Intramolecular Csp³–H/C–C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

The electrochemically enabled α-C(sp³)–H azolation of ketones