Visible-Light-Triggered Sulfonylation/Aryl Migration/Desulfonylation and C–S/Se Bond Formation Reaction: 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate/Selenosulfonates

Liu, Xinyu; Tian, Shi‐Yin; Jiang, Yifan; Rao, Weidong; Wang, Shun‐Yi

doi:10.1021/acs.orglett.1c02981

Cited by 31 publications

(10 citation statements)

References 52 publications

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“…We first synthesized compound 1a, same as before, 7 which did not occur under standard reaction conditions ( of 78%. Then, we experimented with the effect of different solvents on the reaction and found that the reaction was still the best in DMF.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Overcoming Radical Stability Order via DABCO-Triggered Desulfurization: Visible-Light-Promoted 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate

Liu,

Fang,

Rao

et al. 2023

J. Org. Chem.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Overcoming Radical Stability Order via DABCO-Triggered Desulfurization: Visible-Light-Promoted 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate

Liu,

Fang,

Rao

et al. 2023

J. Org. Chem.

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“…We then carried the resulting β‐sulfonyl alkyl heteroarenes for a series of synthetic manipulations. Products 4 and 18 underwent facile β‐sulfone elimination in the presence of strong bases to afford α‐heteroaryl dihydrofurans 41 and 42 in 95 % yields [15] . Catalytic hydrogenation of dihydrofuran 42 with H 2 in the presence of Pd/C gave α‐heteroaryl tetrahydrofuran 43 in 91 % yield [16] .…”

Section: Resultsmentioning

confidence: 99%

Catalyst‐Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible‐Light‐Induced Charge Transfer

Long

Pan

Zhu

et al. 2022

Chemistry A European J

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We report a visible‐light‐induced three‐component sulfonyl‐heteroarylation of vinyl ethers with sulfinates and five‐membered heteroaryl chlorides. This protocol proceeds via electron‐donor‐acceptor (EDA) complexes between sulfinates and heteroaryl chlorides, giving β‐sulfonyl alkyl five‐membered heteroarenes with high efficiency and excellent regioselectivity under mild and catalyst‐free conditions. Utilization of CF3SO2Na or CF2HSO2Na as coupling partners further achieves three‐component fluoromethyl‐arylation of vinyl ethers, furnishing a series of valuable CF3/CF2H‐incorporated alkyl heterocycles under mild conditions.

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“…Thio- and selenosulfonate (PhS–SO 2 Ph and PhSe–SO 2 Ph) are reported to capture carbon radicals, and excellent examples using PhS–SO 2 Ph for the introduction of sulfur-centered functional groups into several building blocks are shown in Scheme 5 . In the presence of radical initiators or under light, the corresponding sulfur-centered radicals are generated from PhS–SO 2 Ph, and sequential radical cascade reactions driven by trapping carbon radicals with them provide pharmaceutical and functional molecule scaffolds in one pot [ 35 , 36 , 37 , 38 , 39 , 40 ].…”

Section: The Group 16 Element (O S Se and Te)-centered Interelement C...mentioning

confidence: 99%

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Yamamoto

2023

Molecules

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In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward the establishment of a resource-recycling society. In organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and the recycling of elemental resources in mind, rather than just only synthesis. Many studies on the construction of frameworks of functional molecules using ionic reactions and transition-metal-catalyzed reactions have been reported, but most of them have focused on the formation of carbon–carbon bonds. However, it is essential to introduce appropriate functional groups at appropriate positions in molecules in order for the molecules to express their functions, and furthermore, the highly selective preparation of multiple functional groups is considered important for the creation of new functional molecules. In this review, we focus on radical reactions with high functional group selectivity and overview the recent progress in practical methods for the simultaneous introduction of multiple functional groups and propose future synthetic strategies that emphasize the recycling of elemental resources and environmental friendliness.

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Visible-Light-Triggered Sulfonylation/Aryl Migration/Desulfonylation and C–S/Se Bond Formation Reaction: 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate/Selenosulfonates

Cited by 31 publications

References 52 publications

Overcoming Radical Stability Order via DABCO-Triggered Desulfurization: Visible-Light-Promoted 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate

Overcoming Radical Stability Order via DABCO-Triggered Desulfurization: Visible-Light-Promoted 1,2,4-Trifunctionalization of Butenyl Benzothiazole Sulfone with Thiosulfonate

Catalyst‐Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible‐Light‐Induced Charge Transfer

Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

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