Rhodium-catalyzed C-H α-fluoroalkenylation/annulation of β-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones

被引：1
作者：
Song, Jia-Lin [1 ,2 ]
Yang, Zi-Feng [3 ]
Fang, Sheng [1 ]
Chen, Wang-Liang [1 ]
Ye, Lian-Bao [1 ]
Liu, Xiang [3 ]
Shu, Bing [1 ,4 ]
机构：
[1] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China
[2] Sun Yat Sen Univ, Sch Chem, Guangzhou 510006, Peoples R China
[3] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China
[4] Guangdong Pharmaceut Univ, Guangdong Prov Key Lab Res & Evaluat Pharmaceut Pr, Guangzhou 510006, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 100期
关键词：
CARBONYL SULFOXONIUM YLIDES; FUNCTIONALIZATION; CYCLIZATION; ACTIVATION; ANNULATION;
D O I：
10.1039/d4cc05621c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Rh(iii)-catalyzed C-H alpha-fluoroalkenylation/annulation of beta-ketosulfoxonium ylides with 2,2-difluorovinyl tosylate/oxadiazolones was realized, which afforded various o-fluoroalkenylation beta-ketosulfoxonium ylides with high Z-selectivity and diverse oxadiazolone fused-isoquinolines. This protocol featured mild conditions, broad substrate scope, and functional-group compatibility. In addition, scale-up synthesis, related applications and preliminary mechanistic explorations were also accomplished.
引用
收藏
页码：15000 / 15003
页数：4
相关论文
共 52 条
  • [1] Cp*Co(iii)-catalyzed C-H amination/annulation cascade of sulfoxonium ylides with anthranils for the synthesis of indoloindolones
    Aher, Yogesh N.
    Pawar, Amit B.
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (58) : 7164 - 7167
  • [2] Metal-catalyzed divergent synthesis from ylides with 3-arylbenzo[d][1,2,3]triazin-4(3H)-ones
    Bao, Mei-Zhu
    Pan, Xiao-Ying
    Wu, Wen-Rong
    Xiao, Lin
    Liu, Jidan
    Liu, Xu-Ge
    Zhang, Shang-Shi
    Zhao, Limin
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (88) : 12928 - 12931
  • [3] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds
    Barday, Manuel
    Janot, Christopher
    Halcovitch, Nathan R.
    Muir, James
    Aissa, Christophe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) : 13117 - 13121
  • [4] Sulfoxonium ylides: simple compounds with chameleonic reactivity
    Bisag, Giorgiana Denisa
    Ruggieri, Silvia
    Fochi, Mariafrancesca
    Bernardi, Luca
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (43) : 8793 - 8809
  • [5] Asymmetric transformations from sulfoxonium ylides
    Caiuby, Clarice A. D.
    Furniel, Lucas G.
    Burtoloso, Antonio C. B.
    [J]. CHEMICAL SCIENCE, 2022, 13 (05) : 1192 - 1209
  • [6] Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes
    Chen, Shao-Yong
    Zheng, Yi-Chuan
    Liu, Xu-Ge
    Song, Jia-Lin
    Shu, Bing
    Zheng, Tao
    Xiao, Lin
    Zhang, Shang-Shi
    Cao, Hua
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3302 - 3309
  • [7] Rh(III)-Catalyzed Cascade Reactions of Sulfoxonium Ylides with α-Diazocarbonyl Compounds: An Access to Highly Functionalized Naphthalenones
    Chen, Xi
    Wang, Muhua
    Zhang, Xinying
    Fan, Xuesen
    [J]. ORGANIC LETTERS, 2019, 21 (08) : 2541 - 2545
  • [8] Chemospecific Cyclizations of α-Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
    Clare, Daniel
    Dobson, Benjamin C.
    Inglesby, Phillip A.
    Aissa, Christophe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (45) : 16198 - 16202
  • [9] Rh(iii)-Catalyzed sequentialortho-C-H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones
    Dong, Yaqun
    Yu, Jin-Tao
    Sun, Song
    Cheng, Jiang
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (49) : 6688 - 6691
  • [10] Copper-Catalyzed α-Arylation of Sulfoxonium Ylides Using Hypervalent Iodine Compounds
    Echemendia, Radell
    To, Avery J.
    Murphy, Graham K.
    Burtoloso, Antonio C. B.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (03) : 396 - 401
123456