Reductive coupling of alkenes with unsaturated imines <i>via</i> a radical pathway

Qi, Jifeng; Tang, Haibin; Chen, Changwei; Cui, Sunliang; Xu, Gang

doi:10.1039/c9qo00653b

Cited by 26 publications

(20 citation statements)

References 59 publications

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“…In 2019, Xu's group reported the reductive coupling/clization reaction between unsaturated imines 41/81 and alkenes 103, and obtained benzofurans, benzothiophenes, and medium-size benzofuranfused heterocycles (Scheme 16e). [73] More importantly, the reaction mechanism is a radical pathway with rarely reported unsaturated imines.…”

Section: α β-Unsaturated Iminesmentioning

confidence: 99%

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Deng

Meng

2020

Chemistry An Asian Journal

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Benzothiophene, benzofuran, indole, and indene derivatives are privileged heterocyclic motifs. These are present in a wide range of bioactive natural products and pharmaceutical drugs and are the subject of materials science research. However, the construction of benzothiophene, benzofuran, indole, and indene frameworks have been long‐standing challenges to organic chemists. In this review, we classify the derivatives of four structures synthesized from 2‐benzylidene‐1‐benzofuran‐3‐one and their analogues in terms of their ring size (from three‐ to ten‐membered) and type (fused or spiro), as well as summarizing the developments of this field. Finally, we discuss the ring opening and 1,4‐addition reactions.

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Section: α β-Unsaturated Iminesmentioning

confidence: 99%

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Deng

Meng

2020

Chemistry An Asian Journal

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“…Based on the previous work using the Fe(III)/silane system to promote hydrogen atom transfer to olefins, the Xu group explored the use of unsaturated imines 70 as radical acceptors in MHAT-driven radical conjugate additions with olefins [ 94 ]. This approach allowed the synthesis of alkylated benzofurans and benzothiophenes ( Scheme 27 ).…”

Section: Reviewmentioning

confidence: 99%

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

Silva¹,

Coelho²

2021

Beilstein J. Org. Chem.

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Olefin double-bond functionalization has been established as an excellent strategy for the construction of elaborate molecules. In particular, the hydroalkylation of olefins represents a straightforward strategy for the synthesis of new C(sp3)–C(sp3) bonds, with concomitant formation of challenging quaternary carbon centers. In the last 20 years, numerous hydroalkylation methodologies have emerged that have explored the diverse reactivity patterns of the olefin double bond. This review presents examples of olefins acting as electrophilic partners when coordinated with electrophilic transition-metal complexes or, in more recent approaches, when used as precursors of nucleophilic radical species in metal hydride hydrogen atom transfer reactions. This unique reactivity, combined with the wide availability of olefins as starting materials and the success reported in the construction of all-carbon C(sp3) quaternary centers, makes hydroalkylation reactions an ideal platform for the synthesis of molecules with increased molecular complexity.

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“…尽管橙酮衍生氮杂二烯参与的化学反应研究较为丰富, 但关于其在自由基反应中的应用还未见报道. 2019 年, 徐刚课题组以 Fe(acac) 3 为催化剂, PhSiH 3 为还原剂, 橙酮衍生氮杂图式 20 橙酮衍生氮杂二烯参与的其他类型转化 Scheme 20 Other transformations of aurone-derived azadienes 二烯作为自由基受体, 通过氢原子转移的自由基反应历程, 实现了这一特殊不饱和亚胺与烯烃之间的还原偶联反应, 为多取代苯并呋喃化合物的合成提供了新思路 (Scheme 20c) [46] .…”

Section: 环化反应unclassified

Recent Progress in the Reactions of Aurone-Derived Azadienes

Yu¹,

Gao²,

Lan³

et al. 2020

Chin. J. Org. Chem.

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Owing to the important physiological and pharmacological activities of benzofuran compounds, the exploration for efficient synthesis methods is of great value and wide application. Aurone-derived azadienes have been identified to be effective reactants in the field of organic synthesis owing to the driving force of aromatization. A large number of reactions based on 1,4-conjugate addition and tandem cyclization have been reported, which exhibited great advantages in the construction of heterocycles with benzofuran skeletons. In this paper, the recent progress in the chemical transformations of aurone-derived azadienens is reviewed, with emphasis on the employed catalytic system and the plausible mechanism of some reactions.

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Reductive coupling of alkenes with unsaturated imines via a radical pathway

Abstract: A reductive coupling of alkenes with unsaturated imines via a radical pathway is described.

Cited by 26 publications

References 59 publications

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Recent Advances in the Cycloaddition Reactions of 2‐Benzylidene‐1‐benzofuran‐3‐ones, and Their Sulfur, Nitrogen and Methylene Analogues

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

Recent Progress in the Reactions of Aurone-Derived Azadienes

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