Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates

被引：25
|
作者：
Li, Yue [1 ]
Yang, Wen [1 ]
Cheng, Guo [1 ]
Yang, Dingqiao [1 ]
机构：
[1] S China Normal Univ, Sch Chem & Environm, Key Lab Theoret Chem Environm, Minist Educ, Guangzhou 510006, Guangdong, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 11期
基金：
中国国家自然科学基金;
关键词：
CROSS-COUPLING REACTION; AZABICYCLIC ALKENES; BICYCLIC OLEFINS; 2-SUBSTITUTED 1,2-DIHYDRO-1-NAPHTHOLS; DIRECT SULFONYLATION; ARYLBORONIC ACIDS; BORONIC ACIDS; OXABENZONORBORNADIENES; ARYL; ARYLATION;
D O I：
10.1021/acs.joc.6b00667
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed syn-stereocontrolled ring opening reactions of oxabenzonorbornadienes with a wide range of sodium arylsulfinates were investigated, affording the desired products in good to excellent yields under an air atmosphere. This protocol provides a low-cost new viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ol with good functional group tolerance. In addition, the cis configuration of 3da was established by X-ray diffraction analysis, and a plausible mechanism, for the ring opening reaction was proposed.
引用
收藏
页码：4744 / 4750
页数：7
相关论文
共 50 条
  • [1] Platinum-catalyzed syn-stereocontrolled ring-opening of oxabicyclic alkenes with sodium arylsulfinates
    Wu, Ruihua
    Yang, Wen
    Chen, Wenkun
    Yang, Dingqiao
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10): : 1921 - 1925
  • [2] Palladium-Catalyzed syn-Stereocontrolled Ring Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides
    Chen, Donghan
    Yao, Yongqi
    Yang, Wen
    Lin, Qifu
    Li, Huanyong
    Wang, Lin
    Chen, Shuqi
    Tang, Yun
    Yang, Dingqiao
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (19): : 12481 - 12489
  • [3] Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides
    Wang, Lin
    Yang, Lili
    Ou, Yunfu
    Xu, Shihai
    Lin, Qifu
    Yang, Dingqiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (12) : 4228 - 4236
  • [4] Mechanistic studies of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc
    Lautens, M
    Hiebert, S
    Renaud, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) : 6834 - 6839
  • [5] Palladium-catalyzed enantioselective ring opening of oxabicyclic alkenes with organozinc halides
    Li, M
    Yan, XX
    Hong, W
    Zhu, XZ
    Cao, BX
    Sun, J
    Hou, XL
    ORGANIC LETTERS, 2004, 6 (16) : 2833 - 2835
  • [6] Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents
    Yang, Dingqiao
    Liang, Ni
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (13) : 2080 - 2086
  • [7] Palladium-catalyzed stereocontrolled ring-opening of 7-oxabenzonorbornadienes with organic carboxylic acids
    Saravanan, Velautham
    Jeganmohan, Masilamani
    CHEMICAL COMMUNICATIONS, 2023, 59 (37) : 5619 - 5622
  • [8] Iridium-Catalyzed Asymmetric Ring-Opening of Oxabicyclic Alkenes with Carboxylic Acids
    Yuhua Long
    Xiaolu Li
    Xuejing Pan
    Dandan Ding
    Xuan Xu
    Xiongjun Zuo
    Dingqiao Yang
    Sanyong Wang
    Chunrong Li
    Catalysis Letters, 2014, 144 : 419 - 433
  • [9] Palladium-Catalyzed Ring-Opening Alkynylation of Cyclopropenones
    Matsuda, Takanori
    Sakurai, Yusuke
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4219 - 4222
  • [10] Iridium-Catalyzed Asymmetric Ring-Opening of Oxabicyclic Alkenes with Carboxylic Acids
    Long, Yuhua
    Li, Xiaolu
    Pan, Xuejing
    Ding, Dandan
    Xu, Xuan
    Zuo, Xiongjun
    Yang, Dingqiao
    Wang, Sanyong
    Li, Chunrong
    CATALYSIS LETTERS, 2014, 144 (03) : 419 - 433
12345