Highly Regioselective Radical Transformation of <i>N</i>-Sulfonyl-1,2,3-triazoles in Air

Li, Zi; Wei, Qinghua; Song, Longlong; Han, Wangyujing; Wu, Xiang; Zhao, Yun; Xia, Fei; Liu, Shunying

doi:10.1021/acs.orglett.9b02269

Cited by 32 publications

(22 citation statements)

References 53 publications

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“…In 2019, Liu, Xia, and co-workers reported a radical chain transformation of 1-sulfonyl-1,2,3-triazoles 35 to yield N 2 -selective alkylation products 37 under air conditions without any catalyst (Scheme 15 ). 27 This efficient radical transformation was promoted by the sulfonyl radical chain reaction. Control experiments and DFT calculation results showed that the new formation of the C–N bond facilitates the homolytic cleavage of the N–S bond, and is affected by steric hindrance, thus giving the desired N 2 -selective products.…”

Section: N 2 -Alkylationmentioning

confidence: 99%

Recent Developments in N2-Selective Functionalizations of 1,2,3-Triazoles

et al. 2022

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The widespread use of 1,2,3-triazole compounds in drugs has resulted in a great interest in the efficient synthesis of N2-substituted 1,2,3-triazoles via post triazole functionalization methods. At present, there are many methods for the synthesis of N1-substituted 1,2,3-triazole compounds, but the development of convenient methods for the N2-selective functionalization of 1,2,3-triazoles remains challenging. In general, the greater stability of the N1 tautomer makes the N2 position a non-preferable reactive site, which has limited the application of 1,2,3-triazoles. In this review, we summarized advances in the direct N2-selective functionalization of 1,2,3-triazoles since 2008.1 Introduction2 N2-Alkylation3 N2-Allylation4 N2-Propargylation5 N2-Alkenylation6 N2-Alkynylation7 N2-Arylation8 Conclusions and Outlook

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Section: N 2 -Alkylationmentioning

confidence: 99%

Recent Developments in N2-Selective Functionalizations of 1,2,3-Triazoles

et al. 2022

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“…但是由于受底物 78 结构复杂的局限, 所报道的产物只有 4 种, 且收率也相对较低 (35%～68%). [44] 报道了一例基于 N-磺酰-1,2,3-三唑 1 的自由基链转移反应. 将底物 1 和四氢呋喃/四氢噻吩 92 简单加热, 经 C(sp 3 )-H 偶联反应可以得到 N -选择性-α-四氢呋喃/噻吩取代三唑衍生物 93 (Scheme 35).…”

Section: 图式 12 N-磺酰三唑和丙二烯基醇的 Rh-催化反应 Scheme 12 Rh-catalyzed Reactionsunclassified

Progress in Synthesis of N-Sulfonyl-1,2,3-triazole and Its Application in Organic Synthesis

Zhang¹,

Xu²,

Zhang³

et al. 2020

Chin. J. Org. Chem.

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Sulfonyl-1,2,3-triazole, an important class of five-membered nitrogen-containing organic compounds, has been found processing widespread application in the synthesis of various nitrogen-containing organic compounds, especially heterocyclic or amino-substituted aromatic rings. The synthetic methods of N-sulfonyl-1,2,3-triazole are introduced. Besides, the progress on constructions of various organic compounds via ring-opening reaction of N-sulfonyl-1,2,3-triazoles as precursor of α-diazoimine and Rh-carbene imine intermediates in the past two years is reviewed.

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“…As such, there is still a demand for the expansion of ways to access new 1,2,3-triazole heterocyclic rings in rapid, efficient, and versatile ways. Triazole rings could serve as important intermediates for numerous important organic transformations [28][29][30]. Diverse applications of these five-membered N-heterocycles are the result of both their easy synthetic procedures and ring functionalization [9,31,32].…”

Section: Introductionmentioning

confidence: 99%

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

Shiri¹,

Amani²,

Mayer‐Gall³

2021

Beilstein J. Org. Chem.

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Diverse strategies for the efficient and attractive synthesis of a wide variety of relevant 1,4,5-trisubstituted 1,2,3-triazole molecules are reported. The synthesis of this category of diverse fully functionalized 1,2,3-triazoles has become a necessary and unique research subject in modern synthetic organic key transformations in academia, pharmacy, and industry. The current review aims to cover a wide literature survey of numerous synthetic strategies. Recent reports (2017–2021) in the field of 1,4,5-trisubstituted 1,2,3-triazoles are emphasized in this current review.

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Highly Regioselective Radical Transformation of N-Sulfonyl-1,2,3-triazoles in Air

Cited by 32 publications

References 53 publications

Recent Developments in N2-Selective Functionalizations of 1,2,3-Triazoles

Recent Developments in N2-Selective Functionalizations of 1,2,3-Triazoles

Progress in Synthesis of N-Sulfonyl-1,2,3-triazole and Its Application in Organic Synthesis

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

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