Catalyst-free photoinduced radical sulfonylation/cyclization of unactivated alkenes toward sulfone-containing quinazolinones

Chen, Si-Yuan; Wang, Ying-Shan; Han, Xian; Zhang, Zhen-Dong; Li, Zhi-Kai; Lu, Dong-Liang; Li, Shaoyu

doi:10.1039/d3qo01974h

Org. Chem. Front.

2024

DOI: 10.1039/d3qo01974h

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Catalyst-free photoinduced radical sulfonylation/cyclization of unactivated alkenes toward sulfone-containing quinazolinones

Si-Yuan Chen,

Ying-Shan Wang,

Xian Han

et al.

Abstract: The difunctionalization of alkenes based on the insertion of sulfur dioxide has been considered to be one of the most straightforward and powerful strategies for the construction of sulfones. Numerous...

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Cited by 3 publications

References 64 publications

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A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO₂)₂, and Benzyl Ether Substituted Alkenes

Zhang,

Cen,

et al. 2024

Adv Synth Catal

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A photoinduced three‐component reaction of thianthrenium salts, DABCO·(SO2)2, and benzyl ether substituted alkenes is developed, affording δ‐hydroxylsulfones with good functional group tolerance. This transformation proceeds through an anti‐Markovnikov hydrosulfonylation of alkenes under a mild reaction condition. Mechanism studies indicates that this reaction undergoes a radical pathway involving sulfur dioxide insertion and 1,5‐hydrogen transfer processes.

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A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO₂)₂, and Benzyl Ether Substituted Alkenes

Zhang,

Cen,

et al. 2024

Adv Synth Catal

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Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam‐Substituted Alkyl Sulfones

Wu,

Zhang,

Yang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAn alkyl radical initiated cyclization/tandem reaction of alkyl bromides and alkyl electrophiles by using potassium metabisulphite (K2S2O5) as a connector is developed for the synthesis of various lactam‐substituted alkyl sulfones. Notably, this process does not require a metal catalyst or metal powder reductant, highlighting its environmentally friendly features. The reaction demonstrates outstanding substrate adaptability and a high tolerance towards diverse functional groups. Furthermore, the biologically active molecules and commercially available drugs with a late‐stage modification are also highly compatible with this transformation. Mechanistic studies revealed that the reaction proceeds through a single‐step process involving intramolecular radical cyclization, "SO2" insertion, and external alkyl incorporation.

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Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

Yang,

Ding,

Yang

et al. 2024

J. Org. Chem.

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Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of Nalkenylacrylamides with sodium sulfinates or sulfonyl hydrazides were described. These methods were carried out under mild, chemical oxidant-free, and transition-metal-free conditions with a broad substrate scope and good functional group tolerance to provide sulfonyl-containing 4-pyrrolin-2-ones, which is readily scalable to the gram scale.

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Catalyst-free photoinduced radical sulfonylation/cyclization of unactivated alkenes toward sulfone-containing quinazolinones

Abstract: The difunctionalization of alkenes based on the insertion of sulfur dioxide has been considered to be one of the most straightforward and powerful strategies for the construction of sulfones. Numerous...

Cited by 3 publications

References 64 publications

A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO₂)₂, and Benzyl Ether Substituted Alkenes

A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO₂)₂, and Benzyl Ether Substituted Alkenes

Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam‐Substituted Alkyl Sulfones

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

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Catalyst-free photoinduced radical sulfonylation/cyclization of unactivated alkenes toward sulfone-containing quinazolinones

Abstract: The difunctionalization of alkenes based on the insertion of sulfur dioxide has been considered to be one of the most straightforward and powerful strategies for the construction of sulfones. Numerous...

Cited by 3 publications

References 64 publications

A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO2)2, and Benzyl Ether Substituted Alkenes

A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO2)2, and Benzyl Ether Substituted Alkenes

Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam‐Substituted Alkyl Sulfones

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides

Contact Info

Product

Resources

About

A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO₂)₂, and Benzyl Ether Substituted Alkenes

A Photoinduced Three‐Component Reaction of Thianthrenium salts, DABCO ⋅ (SO₂)₂, and Benzyl Ether Substituted Alkenes