Visible‐Light‐Mediated Chlorosulfonylative Cyclizations of 1,6‐Enynes

Hou, Hong; Li, Hengxue; Xu, Yilin; Song, Chuan-Qi; Wang, Chunling; Shi, Yao‐Cheng; Han, Ying; Yan, Chao‐Guo; Zhu, Shaoqun

doi:10.1002/adsc.201801157

Cited by 37 publications

(11 citation statements)

References 60 publications

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“…Following a similar strategy but using enynes instead of simple olefins, a cascade cyclization of enynes was recently reported by Hou, Chen, and Zhu’s group. Thus, a new visible-light-mediated photocatalytic chlorotrifluoromethylation and chlorotrichloromethylation of 1,6-enynes 31 in the presence of CX 3 SO 2 Cl (X= F, Cl) is described [ 50 , 51 ]. The process proceeds through an initial radical addition, followed by a cyclization/chlorination sequence.…”

Section: Chloro- and Bromotrifluoromethylationmentioning

confidence: 99%

Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

Escorihuela

Han

et al. 2021

Molecules

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Incorporation of fluorine into organic molecules is a well-established strategy in the design of advanced materials, agrochemicals, and pharmaceuticals. Among numerous modern synthetic approaches, functionalization of unsaturated bonds with simultaneous addition of trifluoromethyl group along with other substituents is currently one of the most attractive methods undergoing wide-ranging development. In this review article, we discuss the most significant contributions made in this area during the last decade (2012−2021). The reactions reviewed in this work include chloro-, bromo-, iodo-, fluoro- and cyano-trifluoromethylation of alkenes and alkynes.

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Section: Chloro- and Bromotrifluoromethylationmentioning

confidence: 99%

Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

Escorihuela

Han

et al. 2021

Molecules

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“…An unconventional example of this reactivity was also reported by Zhu in 2018. 41 The authors managed to merge two aspects of the reactivity of sulfonyl chloride under visible light: the addition to an unsaturated moiety promoting a cascade process and the chlorination of the unsaturated moiety. When terminal alkynes 73 are used, the sulfonyl radical attacks the terminal position instead of the internal carbon of the triple bond.…”

Section: Scheme 28 Photochemical Sequential Chlorosulfonylation Of Olefins 70mentioning

confidence: 99%

“…Scheme 28 Photochemical sequential chlorosulfonylation of 1,4-divinylbenzene An unconventional example of this reactivity was also reported by Zhu, Hou, and Yan in 2018. 42 Two aspects of the reactivity of sulfonyl chloride under visible light were merged: the addition to an unsaturated moiety promoting a cascade process and the chlorination of the unsaturated moiety (Scheme 29). The result is an elegant synthesis of chloroalkyl-substituted cyclic alkenyl sulfones 74 and 75 starting from 1,6-enynes 73 (both terminal and internal alkynes) and sulfonyl chlorides 57 which reacted under visible-light irradiation in the presence of [Ir(dtbbpy)-(ppy) 2 ](PF 6 ) as photosensitizer and water as additive.…”

Section: Review Synthesismentioning

confidence: 99%

Visible Light as the Key for the Formation of Carbon–Sulfur Bonds in Sulfones, Thioethers, and Sulfonamides: An Update

Azzi¹,

Lanfranco²,

Moro³

et al. 2021

Synthesis

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This review summarizes the most relevant advancements made in the photocatalyzed synthesis of sulfones, thioethers and sulfonamides from 2017 to the beginning of 2021. Synthetic strategies towards the construction of sulfur-carbon bonds are discussed together with the proposed reaction mechanisms. Interestingly, sulfured-based functional groups, which are of fundamental importance for the pharmaceutical field, can be assembled by photocatalysis in an easy and straightforward way in milder reaction conditions employing less toxic and expensive sulfur sources in comparison with common strategies

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“…The visible-light-mediated chlorosulfonylative cyclizations of 1,6-enynes with sulfonyl chlorides for the synthesis of chloroalkyl-substituted cyclic alkenyl sulfones was described by Zhu group. [97] The sulfonyl group and chlorine atom all came from sulfonyl chlorides. Oxidative quenching reaction of the excited Ir* catalyst with sulfonyl chlorides could deliver the sulfonyl radical.…”

Section: Sulfonylation With Alkynesmentioning

confidence: 99%

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

et al. 2020

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Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1.

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Visible‐Light‐Mediated Chlorosulfonylative Cyclizations of 1,6‐Enynes

Cited by 37 publications

References 60 publications

Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes

Visible Light as the Key for the Formation of Carbon–Sulfur Bonds in Sulfones, Thioethers, and Sulfonamides: An Update

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

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