Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-<i>a</i>]benzimidazoles

Liu, Yan; Zhang, Niuniu; Xü, Yanli; Chen, Yanyan

doi:10.1021/acs.joc.1c02082

Cited by 22 publications

(12 citation statements)

References 51 publications

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“…The reaction failed in the absence of visible light or lower Thereafter, Xu, Chen, and co-workers reported a similar methodology using 1-allyl-2-ethynylbenzoimidazoles 110 with thiosulfonates 108 and obtained the thiosulfonylated pyrrolo[1,2-a]benzimidazoles 111 in moderate to excellent yields (Scheme 33b). [80] The reaction exhibited a good functional group tolerance and high regioselectivity.…”

Section: Chemcatchemmentioning

confidence: 97%

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

2022

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The 1,n-enynes are potent scaffolds in organic synthesis, providing a state-of-the-art approach for synthesizing various acyclic and carbo-and heterocyclic compounds. Radical cascade cyclization and CÀ H functionalization of 1,n-enynes have gained immense attention in the synthetic community. Significant advancement in this field has been developed over the years, employing harsh and expensive metal catalysts usually associated with intense product purification and unwanted side-products. In this context, the advent of visible light photocatalysis as a mild and efficient approach in the area of 1,nenynes is a welcome step. Herein, we provide an exclusive overview of the recent developments in visible light-assisted manipulation of 1,n-enynes. We have classified the review into 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, and 1,8-enynes, as well as dienyne, and enediyne-based reactions.

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Section: Chemcatchemmentioning

confidence: 97%

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

2022

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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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“…Very recently, Xu, Chen, and co-workers expanded the scope of aryl alkynes to 2-vinyloxy arylalkynes in photoredox ATRA with thiosulfonates, and a variety of thiosulfonated pyrrolo[1,2-a] benzimidazoles were prepared (Scheme 1c). 30 Despite progress, there are still some common drawbacks in the previous reports, jeopardizing the application of this powerful tool on cysteine bioconjugation. Synthesis of S-alkyl alkylthiosulfonates, a class of molecules sensitive to air and moisture, typically is not trivial, which suffers from tedious operation and low yields.…”

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confidence: 99%

“…In 2020, our group exploited thiosulfonates as a thiyl radical precursor while switching the light source and photocatalyst to white LED and Eosin Y, respectively (Scheme b), and developed a highly stereoselective approach altering the regioselectivity compared to Xu’s report. Very recently, Xu, Chen, and co-workers expanded the scope of aryl alkynes to 2-vinyloxy arylalkynes in photoredox ATRA with thiosulfonates, and a variety of thiosulfonated pyrrolo[1,2- a ] benzimidazoles were prepared (Scheme c) …”

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confidence: 99%

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Tagging Peptides with a Redox Responsive Fluorescent Probe Enabled by Photoredox Difunctionalization of Phenylacetylenes with Sulfinates and Disulfides

Liu

Peng

et al. 2022

JACS Au

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Herein, we describe a photoredox three-component atom-transfer radical addition (ATRA) reaction of aryl alkynes directly with dialkyl disulfides and alkylsulfinates, circumventing the utilization of chemically unstable and synthetically challenging S-alkyl alkylthiosulfonates as viable addition partners. A vast array of (E)-βalkylsulfonylvinyl alkylsulfides was prepared with great regio-and stereoselectivity. Moreover, this powerful tactic could be employed to tag cysteine residues of complex polypeptides in solution or on resin merging with solid phase peptide synthesis (SPPS) techniques. A sulfonyl-derived redox responsive fluorescent probe could be conveniently introduced on the peptide, which displays green fluorescence in cells while showing blue fluorescence in medium. The photophysical investigations reveal that the red shift of the emission fluorescence is attested to reduction of carbonyl group to the corresponding hydroxyl moiety. Interestingly, the fluorescence change of tagged peptide could be reverted in cells by treatment of H 2 O 2 , arising from the reoxidation of hydroxyl group back to ketone by the elevated level of reactive oxygen species (ROS).

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Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles

Cited by 22 publications

References 51 publications

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

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

Tagging Peptides with a Redox Responsive Fluorescent Probe Enabled by Photoredox Difunctionalization of Phenylacetylenes with Sulfinates and Disulfides

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