Regio- and Stereoselective Photoredox-Catalyzed Atom Transfer Radical Addition of Thiosulfonates to Aryl Alkynes

Peng Zhiyuan; Yin Haolin; Zhang Hui; Jia Tiezheng

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Regio- and Stereoselective Photoredox-Catalyzed Atom Transfer Radical Addition of Thiosulfonates to Aryl Alkynes

机译：测定和立体选择性的光针催化的原子转移到硫代硫酸酯的硫代磺酸盐

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Despite extensive investigations, altering the regioselectivity of atom transfer radical addition (ATRA) to alkynes remains a highly desirable yet unachieved challenge. Guided by computational predictions, thiosulfonates were found herein as a tunable radical precursor for thiyl radicals instead of well-recognized sulfonyl radicals. Merging such a finding with ATRA to phenylacetylenes leads to a highly regio- and stereoselective approach to (E)-beta-arylsulfonylvinyl sulfides. This protocol is feathered by mild conditions, low photocatalyst loading, no transition-metal catalyst required, and broad functional group compatibility. The successful application of our protocol in the late-stage functionalization of bioactive natural product derivatives demonstrates its synthetic utility. Mechanistic studies corroborate the photoredox-catalyzed ATRA pathway and reveal the pivotal role of thiyl radical, to which unprecedented regioselectivity was attributed.

机译：尽管进行了广泛的调查，改变原子转移激进添加（ATRA）至炔虫的区域仍然是一个非常理想的尚未解析的挑战。通过计算预测引导，本文发现硫代磺酸盐作为硫基的可调谐自由基前体，而不是良好识别的磺酰基。将这种发现与ATRA合并到苯乙酰基上导致高度的（e） - 亚芳基磺酰乙烯基硫乙烯嘧啶的高度测定和立体选择性方法。该方案通过温和条件，低光催化剂负载，无需过渡金属催化剂，以及广泛的官能团相容性进行羽毛。我们在生物活性天然产物衍生物的后期功能化中的成功应用证明了其合成效用。机械研究证实了光致毒催化的ATRA途径，揭示了巯基的关键作用，归因于前所未有的区域选择性。

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《Organic letters》 |2020年第15期|共5页
作者
Peng Zhiyuan; Yin Haolin; Zhang Hui; Jia Tiezheng;
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Southern Univ Sci &

Technol Shenzhen Grubbs Inst Dept Chem Shenzhen 518055 Guangdong Peoples R China;

Univ Penn Dept Chem Roy &

Diana Vagelos Labs Philadelphia PA 19104 USA;

Southern Univ Sci &

Technol Shenzhen Grubbs Inst Dept Chem Shenzhen 518055 Guangdong Peoples R China;

Southern Univ Sci &

Technol Shenzhen Grubbs Inst Dept Chem Shenzhen 518055 Guangdong Peoples R China;

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正文语种 eng
中图分类有机化学;
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1. Regio- and Stereoselective Photoredox-Catalyzed Atom Transfer Radical Addition of Thiosulfonates to Aryl Alkynes [J] . Peng Zhiyuan, Yin Haolin, Zhang Hui, Organic letters . 2020,第15期

机译：测定和立体选择性的光针催化的原子转移到硫代硫酸酯的硫代磺酸盐
2. Di-tert-Butyl Peroxide-Mediated Atom-Transfer Radical Addition of 2-Chlorodithiane to Aryl Alkynes under Mild Conditions [J] . Lai Junshan, Tian Lixia, Liang Yongping, Chemistry: A European journal . 2015,第41期

机译：在温和条件下，过氧化二叔丁基介导的2-氯二噻吩原子转移自由基加成到芳基炔烃上
3. Nucleophilic Addition versus SNAr Study: Chemo-, Regio- and Stereoselective Hydrothiolation of Haloaryl Alkynes over S-Arylation of Aryl Halides [J] . Patel Monika, Saunthwal Rakesh K., Dhaked Devendra K., Asian Journal of Organic Chemistry . 2015,第9期

机译：亲核加成与SNAr研究：卤代芳基炔烃的化学，区域和立体选择性氢硫醇化作用比芳基卤化物的S-化
4. Construction of Carbon Skeletons by Transition Metal-Catalyzed Regio- and Stereoselective Addition of Carbon-Chalcogen Bonds to Alkynes and Allenes [C] . Masashi Tovofuku, Erika Murase, Atsushi Okada Symposium on Organometallic Chemistry . 2008

机译：通过过渡金属催化的碳骨架施工碳骨架和立体选择性加入碳 - 硫醇键与炔烃和艾伦
5. Regio- and stereoselective additions to azomethines: Free radical cyclizations and chiral Bronsted acid catalyzed reactions of imines. [D] . Nugent, Benjamin M. 2006

机译：偶氮甲胺的区域和立体选择性加成：自由基环化和手性布朗斯台德酸催化的亚胺反应。
6. Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions [O] . Dat Phuc Tran, Yuki Sato, Yuki Yamamoto, 2021

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7. Light-Induced Intramolecular Iodine-Atom Transfer Radical Addition of Alkyne: An Approach from Aryl Iodide to Alkenyl Iodide [O] . -1

机译：光诱导的分子内碘 - 原子转移自由基加入炔烃：从芳基碘化给链烯基碘的方法

Regio- and Stereoselective Photoredox-Catalyzed Atom Transfer Radical Addition of Thiosulfonates to Aryl Alkynes

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