Diastereoselective 2,3-diazidation of indoles via copper(II)-catalyzed dearomatization

Liu, Jiang; Fang, Zhongjin; Liu, Xin; Dou, Yandong; Jiang, Jianze; Zhang, Fang-Fang; Qu, Jiaojiao; Zhu, Qing

doi:10.1016/j.cclet.2019.10.035

Cited by 28 publications

(14 citation statements)

References 34 publications

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“…This strategy smartly avoided the N 1/ N 2 regioselective problem in conventional alkylation reaction of benzotriazoles. Beside the aforementioned examples, this transition-metal-free aryne-azide [3 + 2] cycloaddition protocol turned out to be quite general and has found a broad spectrum of synthetic applications. − …”

Section: Pericyclic Reactionsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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Section: Pericyclic Reactionsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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“…Later, in 2020, the Zhu group developed the directing group-assisted highly diastereoselective diazidation of indoles 142 via the copper(II)-catalyzed dearomatization of indoles using a PhI(OAc) 2 -TMSN 3 reagent system under aqueous conditions. This methodology enables the direct synthesis of a variety of 2,3-diazido indolines 143 in high yields with high diastereoselectivity under relatively mild conditions (Scheme b) . Whereas Liu group achieved the oxidative diazidation of alkenes using TMSN 3 and NFSI as the N 3 source and oxidant, respectively under palladium catalysis.…”

Section: Azidation Of C–c Multiple Bondsmentioning

confidence: 97%

“…This methodology enables the direct synthesis of a variety of 2,3diazido indolines 143 in high yields with high diastereoselectivity under relatively mild conditions (Scheme 36b). 164 Whereas Liu group achieved the oxidative diazidation of alkenes using TMSN 3 and NFSI as the N 3 source and oxidant, respectively under palladium catalysis. The reaction tolerated both styrene and unactivated alkenes.…”

Section: Rearomatization Along With the Extrusion Of Somentioning

confidence: 99%

New Strategies for the Synthesis of Aliphatic Azides

Sivaguru

Ning

2021

Chem. Rev.

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Aliphatic azides are a versatile class of compounds found in a variety of biologically active pharmaceuticals. These compounds are also recognized as useful precursors for the synthesis of a range of nitrogen-based scaffolds of therapeutic drugs, biologically active compounds, and functional materials. In light of the growing importance of aliphatic azides in both chemical and biological sciences, a vast array of synthetic strategies for the preparation of structurally diverse aliphatic azides have been developed over the past decades. However, to date, this topic has not been the subject of a dedicated review. This review aims to provide a concise overview of modern synthetic strategies to access aliphatic azides that have emerged since 2010. The discussed azidation reactions include (a) azidation of C–C multiple bonds, (b) azidation of C–H bonds, (c) the direct transformation of vinyl azides into other aliphatic azides, and (d) miscellaneous reactions to access aliphatic azides. We critically discuss the synthetic outcomes and the generality and uniqueness of the different mechanistic rationale of each of the selected reactions. The challenges and potential opportunities of the topic are outlined.

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“…4 20 : 1) (Scheme 11). 98 In the catalytic cycle, a stable five-membered Cu(II)-complex is formed via subsequent coordination with the directing group and regioselective C-H activation at the C-2 position of the N-substituted indole. Meanwhile, N 3 formed by the reaction of PIDA and TMSN 3 is captured by the Cu(II)complex to generate a Cu(III)-N 3 intermediate.…”

Section: Functionalization Of Alkenesmentioning

confidence: 99%