Pd-Catalyzed/Ligand-Controlled Regioselective Asymmetric Hydrosulfonylation of Alkylallenes or Arylallenes

被引:0
|
作者
Wu, Jing [1 ,2 ,3 ]
Wang, Boyi [1 ,2 ,3 ]
Zou, Jinghan [1 ,2 ,3 ]
Guo, Xinman [1 ,2 ,3 ]
Chang, Weixing [1 ,2 ,3 ]
Liu, Lingyan [1 ,2 ,3 ]
Cao, Xiaohui [4 ]
Li, Jing [1 ,2 ,3 ,5 ]
机构
[1] Nankai Univ, Natl Engn Res Ctr Pesticide, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Natl Engn Res Ctr Pesticide, Tianjin 300071, Peoples R China
[3] Nankai Univ, Coll Chem, Tianjin 300071, Peoples R China
[4] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China
[5] Collaborat Innovat Ctr Chem Sci Engn Tianjin, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
ALLENES SYNTHESIS; TERMINAL ALLENES; C-C; ALLYLATION; REGIODIVERGENT; HYDROALKOXYLATION; ALKOXYALLENES; CONSTRUCTION; ACCESS;
D O I
10.1021/acs.orglett.4c04259
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The metal-catalyzed hydrofunctionalization reaction of allenes is an efficient approach for the construction of new allyl compounds. This work described a palladium-catalyzed/ligand-controlled asymmetric hydrosulfonylation of simple alkylallenes and arylallenes in the presence of Pd2dba3. Using a Josiphos or Segphos ligand, the alkylallenes or arylallenes could render the corresponding branched chiral allylsulfones with high yields and high enantioselectivities up to 90% and 99% ee, respectively.
引用
收藏
页码:1350 / 1355
页数:6
相关论文
共 50 条
  • [1] Ligand-Controlled Regioselective Pd-Catalyzed Diamination of Alkenes
    Liu, Xiaojian
    Hou, Chuanqi
    Peng, Yiyuan
    Chen, Pinhong
    Liu, Guosheng
    ORGANIC LETTERS, 2020, 22 (23) : 9371 - 9375
  • [2] Highly Ligand-Controlled Regioselective Pd-Catalyzed Aminocarbonylation of Styrenes with Aminophenols
    Xu, Tongyu
    Sha, Feng
    Alper, Howard
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (20) : 6629 - 6635
  • [3] Ligand-controlled regiodivergence in Pd-catalyzed coupling of azlactones with isoprene
    Zhang, Wei -Nan
    Hu, Yan-Cheng
    Liu, Yan
    Wang, Xiao-Yu
    Zhao, Ying-Ying
    Chen, Qing-An
    CELL REPORTS PHYSICAL SCIENCE, 2024, 5 (04):
  • [4] Regiodivergent and stereospecific Pd-catalyzed addition of alkynes to allenamides: Ligand-controlled hydro- and carbopalladation
    Park, Jin Kyoon
    Pradhan, Tapas R.
    Kim, Hong Won
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [5] Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes
    Jiang, Yanxin
    Cheng, Kwai Wun
    Yang, Zhiping
    Wang, Jun
    CHINESE CHEMICAL LETTERS, 2025, 36 (05)
  • [6] Interplay of Ligand-Controlled Reaction Pathways: DFT Analysis of Mechanisms and Selectivities in Pd-Catalyzed Semireduction of Allenamides
    Ma, Ji
    Qi, Simeng
    Yan, Guowei
    Kirillov, Alexander M.
    Yang, Lizi
    Fang, Ran
    MOLECULAR CATALYSIS, 2024, 560
  • [7] Mechanistic Origin of Ligand-Controlled Regioselectivity in Pd-Catalyzed C-H Activation/Arylation of Thiophenes
    Tang, Shi-Ya
    Guo, Qing-Xiang
    Fu, Yao
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (49) : 13866 - 13876
  • [8] Ligand-controlled copper-catalyzed regioselective hydroborylation and borylstannylation of allensulfonamides
    Lee, Haeeun
    Park, Jin Kyoon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [9] Ligand-Controlled Highly Regioselective and Asymmetric Hydrogenation of Quinoxalines Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes
    Urban, Slawomir
    Ortega, Nuria
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (16) : 3803 - 3806
  • [10] Pd-Catalyzed Regioselective Asymmetric Addition Reaction of Unprotected Pyrimidines to Alkoxyallene
    Kang, Soyeong
    Jang, Seok Hyeon
    Lee, Juyeol
    Kim, Dong-gil
    Kim, Mijin
    Jeong, Wook
    Rhee, Young Ho
    ORGANIC LETTERS, 2017, 19 (17) : 4684 - 4687