Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes

被引:83
|
作者
Morimoto, Keisuke [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 22期
关键词
C-H BOND; CARBON-HYDROGEN BONDS; INTERNAL ALKYNES; ACTIVATION; FUNCTIONALIZATION; CLEAVAGE; HETEROCYCLES; ARYLATION; ALKENES; ROUTE;
D O I
10.1021/jo201923d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The straightforward synthesis of isochromene derivatives and related cyclic ethers is achieved by the rhodium-catalyzed oxidative coupling of alpha,alpha-disubstituted benzyl and allyl alcohols with alkynes. The hydroxy groups effectively act as the key function for the regioselective C-H bond cleavage.
引用
收藏
页码:9548 / 9551
页数:4
相关论文
共 50 条
  • [31] Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage
    Mochida, Satoshi
    Umeda, Nobuyoshi
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY LETTERS, 2010, 39 (07) : 744 - 746
  • [32] Rhodium-Catalyzed Decarboxylative and Dehydrogenative Coupling of Maleic Acids with Alkynes and Alkenes
    Itoh, Masaki
    Shimizu, Masaki
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22): : 11427 - 11432
  • [33] Rhodium-Catalyzed Asymmetric Synthesis of Spirosilabifluorene Derivatives
    Kuninobu, Yoichiro
    Yamauchi, Kanae
    Tamura, Naoya
    Seiki, Takayuki
    Takai, Kazuhiko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1520 - 1522
  • [34] Rhodium-catalyzed coupling reaction of 2-vinylpyridines with allyl ethers
    Lim, YG
    Han, JS
    Koo, BT
    Kang, JB
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1999, 20 (09) : 1097 - 1100
  • [35] Rhodium-Catalyzed Functionalization and Annulation of N-Aryl Phthalazinediones with Allyl Alcohols
    Naharwal, Sushma
    Dinkar Kharat, Narendra
    Bajaj, Kiran
    Panda, Siva S.
    Sakhuja, Rajeev
    CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (23)
  • [36] Rhodium-catalyzed synthesis of indenols by regioselective coupling of alkynes with ortho-carbonylated arylboronic acids
    Shintani, R
    Okamoto, K
    Hayashi, T
    CHEMISTRY LETTERS, 2005, 34 (09) : 1294 - 1295
  • [37] Chemoselective Synthesis of Naphthylamides and Isoquinolinones via Rhodium-Catalyzed Oxidative Dehydrogenative Annulation of Benzamides with Alkynes
    Shi, Zhuangzhi
    Tang, Conghui
    Jiao, Ning
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) : 2695 - 2700
  • [38] Synthesis of Substituted Indene Derivatives via Silver-catalyzed Annulative 1:1 Coupling of Secondary Benzyl Alcohols with Alkynes
    Morisaka, Hideaki
    Hirosawa, Keishi
    Inai, Yasuhito
    Usuki, Yoshinosuke
    Satoh, Tetsuya
    CHEMISTRY LETTERS, 2021, 50 (03) : 456 - 458
  • [39] Rhodium-catalyzed selective oxidative coupling of 7-azaindoles
    Li, Shuai-Shuai
    Wang, Cheng-Qi
    Li, Wei-Huan
    Zhang, Xiao-Mei
    Dong, Lin
    TETRAHEDRON, 2016, 72 (20) : 2581 - 2586
  • [40] Rhodium-Catalyzed Oxidative Coupling of Potassium Vinyltrifluoroborate with Arenes: A Direct Access to Functionalized Styrene Derivatives
    Ma, Wenbo
    Wang, Yang
    Li, Bo
    Zhou, Yunhao
    Xu, Yue
    Sun, Yanan
    Gu, Linghui
    Cheng, An
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (22) : 3881 - 3887