Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

Cheng, Fei; Wang, Lili; Mao, Yuanhu; Dong, Yong‐Xi; Liu, Bin; Zhu, Guoqi; Yang, Yuanyong; Guo, Bing; Tang, Lei; Zhang, Ji-Quan

doi:10.1021/acs.joc.1c00284

Cited by 15 publications

(6 citation statements)

References 36 publications

(50 reference statements)

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“…The selenolactonization of alkenoic acids using diselenides, which are stable and easily accessible reagents, has become increasingly popular. Recently, the Liu and Zhang groups reported the selenolactonization of alkenoic acids using diselenides with photo‐ and metal‐catalysts (Scheme 1a and 1b) [6d–e] . These selenolactonization reactions involved a single electron transfer redox process.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Oxidative Selenolactonization of Alkenoic Acids with Diselenides: Synthesis of Selenated γ‐Lactones

2021

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Section: Methodsmentioning

confidence: 99%

Electrochemical Oxidative Selenolactonization of Alkenoic Acids with Diselenides: Synthesis of Selenated γ‐Lactones

2021

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“…Recently, Tang, Zhang, and coworkers published a process of lactonization of enoic acids catalyzed by FeCl 3 in the presence of diorganyl dichalcogenides to access chalcogendecorated γ-lactones and δ-lactones 31 through a simple, atom-economic, and environmentally friendly protocol [59]. By the reaction optimization study, the authors set the best reaction condition by mixing the starting materials in the presence of FeCl 3 (10 mol%), KI (0.5 equiv.…”

Section: O-based Heterocyclesmentioning

confidence: 99%

Recent Approaches in Transition Metal-Catalyzed Chalcogenative Heteroannulation of Alkenes and Alkynes

Gutterres,

Anjos,

Santos

et al. 2023

Catalysts

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Organochalcogen-bearing heterocycles are important scaffolds in compounds under the spotlight of scientific interest in optoelectronic fields and for biological applications. The use of transition metals has been a versatile and reliable way to carry out the synthesis of these molecules efficiently, delivering products in high yields and with a wide functional diversity. In the last 10 years, many classes of heterocycles have been synthesized under the cyclization reaction of acyclic alkenes and alkynes with the incorporation of a chalcogen atom on its structure. Transition metal catalysts including Cu, Co, Pd, Ni, In, Ag, and Fe salts have been used in the development of new methodologies, the expansion of substrate scope, and mechanistic studies. This review provides an overview of these recent approaches with the aim of being a useful resource for interested researchers in this area.

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“…Compared to Guo’s and Li’s seminal reports ( Scheme 19 ), the authors propose the intramolecular cyclization proceeds via the nucleophilic attack of a brominated or cationic benzylic position rather than a radical cyclization. In 2021, Tang and Zhang demonstrated a similar radical annulation of unsaturated carboxylic acids with disulfides for the synthesis of γ-lactones [ 146 ].…”

Section: Reviewmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

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Iron-Catalyzed Radical Annulation of Unsaturated Carboxylic Acids with Disulfides for the Synthesis of γ-Lactones

Cited by 15 publications

References 36 publications

Electrochemical Oxidative Selenolactonization of Alkenoic Acids with Diselenides: Synthesis of Selenated γ‐Lactones

Electrochemical Oxidative Selenolactonization of Alkenoic Acids with Diselenides: Synthesis of Selenated γ‐Lactones

Recent Approaches in Transition Metal-Catalyzed Chalcogenative Heteroannulation of Alkenes and Alkynes

Iron-catalyzed domino coupling reactions of π-systems

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