Iridium-Catalyzed C5-Regioselective Esterification of Dienyl Alcohols with Carboxylic Acids

被引：2
|
作者：
Chen, Jiadong [1 ]
Zhang, Yulu [1 ]
Tang, Shengbiao [1 ]
Shao, Ying [1 ]
Sun, Jiangtao [1 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv, Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 32期
基金：
中国国家自然科学基金;
关键词：
allylic substitution; carboxylic acids; esterification; iridium; regioselective; ALLYLIC SUBSTITUTION-REACTIONS; ALKYLATION;
D O I：
10.1002/ejoc.202300605
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
One-step process for the preparation of a 1,3-dienyl-5-ester motif from readily available substrate remains a challenging work in organic synthesis. We herein report the first example of C5-regioselective esterification of unactivated dienyl alcohols, using free carboxylic acids as nucleophiles under mild conditions, providing a series of 1,3-dienyl-5-ester compounds in excellent regioselectivity and E-selectivity.
引用
下载
收藏
页数：4
相关论文
共 50 条
  • [31] Iridium-Catalyzed Synthesis of ω-Hydroxy Homoallylic Alcohols
    Obora, Yasushi
    Sawaguchi, Takuya
    Tsubakimoto, Keiko
    Yoshida, Hiroshi
    Ogawa, Shinji
    Hatanaka, Shintaro
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2115 - 2119
  • [32] Iridium(i)-catalyzed hydration/esterification of 2-alkynylphenols and carboxylic acids
    Zeng, Linwei
    Chen, Renjie
    Zhang, Chen
    Xie, Hujun
    Cui, Sunliang
    CHEMICAL COMMUNICATIONS, 2020, 56 (20) : 3093 - 3096
  • [33] Enantio- and Regioselective Iridium-Catalyzed Allylic Hydroxylation
    Gaertner, Martin
    Mader, Steffen
    Seehafer, Kai
    Helmchen, Guenter
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) : 2072 - 2075
  • [34] Direct Esterification of Carboxylic Acids with Alcohols Catalyzed by Iron(III) Acetylacetonate Complex
    Weng, Shiue-Shien
    Chen, Fong-Kuang
    Ke, Chih-Shueh
    SYNTHETIC COMMUNICATIONS, 2013, 43 (19) : 2615 - 2621
  • [35] Dehydrative esterification of carboxylic acids with alcohols catalyzed by polymer-supported sulfonic acids in water
    Manabe, K
    Kobayashi, S
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 270 - 273
  • [36] Iridium-catalyzed conversion of alcohols into amides via oximes
    Owston, Nathan A.
    Parker, Alexandra J.
    Williams, Jonathan M. J.
    ORGANIC LETTERS, 2007, 9 (01) : 73 - 75
  • [37] Iridium-catalyzed α-Alkylation of Acetonitrile with Primary and Secondary Alcohols
    Sawaguchi, Takuya
    Obora, Yasushi
    CHEMISTRY LETTERS, 2011, 40 (09) : 1055 - 1057
  • [38] Iridium-Catalyzed α-Alkylation of Acetates with Primary Alcohols and Diols
    Iuchi, Yosuke
    Obora, Yasushi
    Ishii, Yasutaka
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) : 2536 - +
  • [39] Iridium-Catalyzed Regioselective Synthesis of Trifluoromethylated Isocoumarins through Annulation of Benzoic Acids with Trifluoromethylated Alkynes
    Liu, Guangyuan
    Kuang, Guanghua
    Zhang, Xingxing
    Lu, Naihao
    Fu, Yang
    Peng, Yiyuan
    Zhou, Yirong
    ORGANIC LETTERS, 2019, 21 (09) : 3043 - 3047
  • [40] Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols
    Mantilli, Luca
    Gerard, David
    Torche, Sonya
    Besnard, Celine
    Mazet, Clement
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5143 - 5147
12345