Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis with a Catalytic Amount of Silane Reagent

Zhang Xiao-Yu; Wu Xiao-Yun; Zhang Bo; Wei Yin; Shi Min

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Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis with a Catalytic Amount of Silane Reagent

机译：通过光致毒剂催化硅烷试剂的光毒剂催化，甲基丙烯酰胺/乙烯基磺酰胺 - 连接的烷基二烷基丙烷烷基含有丙烯酰胺/乙烯基胺酰胺 - 连接的烷基键合。

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摘要

A silyl radical-mediated carbocyclization of acrylamide-/vinyl sulfonamide-attached alkylidenecyclopropanes via photoredox catalysis with a catalytic amount of silane reagent is reported in this paper. With this protocol, a highly efficient synthesis for the construction of lactam- and sultam-containing polycyclic derivatives in 63-95% yields was achieved with a broad substrate scope. A reasonable reaction mechanism was proposed based on control experiments, where the catalytic amount of tris(trimethylsilyl)silane was used as the radical-based reagent.

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来源
《ACS catalysis》 |2021年第8期|共9页
作者
Zhang Xiao-Yu; Wu Xiao-Yun; Zhang Bo; Wei Yin; Shi Min;
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作者单位

East China Univ Sci &

Technol Sch Chem &

Mol Engn Key Lab Adv Mat Shanghai 200237 Peoples R China;

East China Univ Sci &

Technol Sch Chem &

Mol Engn Key Lab Adv Mat Shanghai 200237 Peoples R China;

East China Univ Sci &

Technol Sch Chem &

Mol Engn Key Lab Adv Mat Shanghai 200237 Peoples R China;

Chinese Acad Sci Univ Chinese Acad Sci Ctr Excellence Mol Synth State Key Lab Organometall Chem Shanghai Inst Org Shanghai 200032 Peoples R China;

East China Univ Sci &

Technol Sch Chem &

Mol Engn Key Lab Adv Mat Shanghai 200237 Peoples R China;

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原文格式 PDF
正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
silyl radical; photochemistry; acrylamide-/vinyl sulfonamide-attached alkylidenecyclopropanes; ring-opening; lactam- and sultam-containing polycyclic derivatives;

机译：甲硅烷基团;光化学;丙烯酰胺 - /乙烯基磺酰胺 - 连接的烷基癸酰丙烷;开环;含有含酸内酰胺和肥皂水的多环衍生物;

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专利

1. Cyclic Iodine Reagents Enable Allylic Alcohols for Alkyl Boronate Addition/Rearrangement by Photoredox Catalysis [J] . Mingshang Liu, Hanchu Huang, Yiyun Chen 中国化学（英文版） . 2018,第012期
2. Radical-Mediated Silyl- and Germyldesulfonylation of Vinyl and (α-Fluoro)vinyl Sulfones: Application of Tris(trimethylsilyl)silanes and Tris(trimethylsilyl)germanes in Pd-Catalyzed Couplings [J] . Stanislaw F. Wnuk, Pedro I. Garcia Jr., Zhizhong Wang Organic letters . 2004,第12期

机译：自由基介导的乙烯基和（α-氟）乙烯基砜的甲硅烷基和Gerylyldesulfonylation：三（三甲基甲硅烷基）硅烷和三（三甲基甲硅烷基）锗烷在Pd催化偶联中的应用
3. Cascade cyclization reactions of alkylidenecyclopropanes for the construction of polycyclic lactams and lactones by visible light photoredox catalysis [J] . Organic Chemistry Frontiers . 2020,第2期

机译：亚烷基羰基丙烷的梯形环化反应通过可见光光致氧催化通过可见光阳性催化含有圆环内酰胺和内酯的构建
4. Mannich-type allylic C-H functionalization of enol silyl ethers under photoredox-thiol hybrid catalysis [J] . Tsubasa Nakashima, Kohsuke Ohmatsu, Takashi Ooi Organic & biomolecular chemistry . 2021,第1期

机译：Cherox-Thiol杂交催化下烯醇型烯醇型烯丙基C-H官能化
5. Direct Allylic C?H Alkylation of Enol Silyl Ethers Enabled by Photoredox-Bronsted Base Hybrid Catalysis [C] . NAKASHIMA Tsubasa, OHMATSU Kohsuke, OOI Takashi 日本化学会春季年会講演予稿集 . 2018

机译：直接烯丙基C-H烷基化烯醇甲硅烷基醚化的光毒氧化物基杂交催化催化
6. Preparation of Allyl and Vinyl Silanes via the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction [O] . Jesse R. McAtee, Sara E. S. Martin, Derek T. Ahneman, -1

机译：通过钯催化的末端烯烃的甲硅烷基制备烯丙基和乙烯基硅烷：甲硅烷基 - 静脉反应
7. Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis with a Catalytic Amount of Silane Reagent [O] . -1

机译：含甲硅烷基介导的丙烯酰胺/乙烯基磺酰胺烷基烷基羰基丙烷通过光致毒剂催化的硅烷试剂的催化量
8. Reaction of Secondary and Tertiary Alkyllithium Reagents with Vinyl Di- and Trisiloxanes. Synthesis of alpha-Silyl Silanols. [R] . Firgo, H. A., Weber, W. P. 1981

机译：二级和三级烷基锂试剂与乙烯基二硅氧烷和三硅氧烷的反应。 α-甲硅烷基硅烷醇的合成。

Silyl Radical-Mediated Carbocyclization of Acrylamide-/Vinyl Sulfonamide-Attached Alkylidenecyclopropanes via Photoredox Catalysis with a Catalytic Amount of Silane Reagent

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