Carbon dioxide-promoted palladium-catalyzed dehydration of primary allylic alcohols: access to substituted 1,3-dienes

被引:15
|
作者
Huang, Yan-Kai [1 ]
Zhang, Wen-Zhen [1 ]
Zhang, Ke [1 ]
Wang, Wen-Le [1 ]
Lu, Xiao-Bing [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
Carbon dioxide;
D O I
10.1039/d0qo01465f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3-Dienes are versatile synthons and important monomers. Herein we report a carbon dioxide promoted dehydration reaction of primary allylic alcohols to produce substituted 1,3-dienes in good yields. Taking advantage of carbon dioxide as a promoter to facilitate the alcoholic C-O bond cleavage via the formation of an allylic bicarbonate ester, this reaction proceeds under mild conditions.
引用
收藏
页码:941 / 946
页数:6
相关论文
共 50 条
  • [1] On the nature of the palladium-catalyzed elimination of allylic carbonates to form 1,3-dienes
    Takacs, JM
    Lawson, EC
    Clement, F
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 633 - ORGN
  • [2] PALLADIUM-CATALYZED ANNULATION OF OXYGEN-SUBSTITUTED 1,3-DIENES
    LAROCK, RC
    GUO, LQ
    SYNLETT, 1995, (05) : 465 - 466
  • [3] PALLADIUM-CATALYZED HETEROANNULATION OF 1,3-DIENES BY FUNCTIONALLY SUBSTITUTED ARYL HALIDES
    LAROCK, RC
    BERRIOSPENA, N
    NARAYANAN, K
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11): : 3447 - 3450
  • [4] THE PALLADIUM-CATALYZED ADDITION OF HEXAMETHYLDITIN TO 1,3-DIENES
    MITCHELL, TN
    KOWALL, B
    KILLING, H
    NETTELBECK, C
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 439 (01) : 101 - 105
  • [5] Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes
    Shen, Hong-Cheng
    Wu, Yu-Feng
    Zhang, Ying
    Fan, Lian-Feng
    Han, Zhi-Yong
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2372 - 2376
  • [6] Palladium-Catalyzed Enantioselective Hydrohydrazonation of 1,3-Dienes
    Sun, Shaozi
    Zhang, Qinglong
    Zi, Weiwei
    ORGANIC LETTERS, 2023, 25 (47) : 8397 - 8401
  • [7] Palladium-catalyzed asymmetric hydrosilylation of 1,3-dienes
    Han, Jin Wook
    Hayashi, Tamio
    TETRAHEDRON-ASYMMETRY, 2010, 21 (18) : 2193 - 2197
  • [8] CARBON-DIOXIDE PROMOTED TELOMERIZATION OF 1,2-DIENES AND 1,3-DIENES WITH BENZENESULFINATE CATALYZED BY PALLADIUM(0)
    INOUE, Y
    HASHIMOTO, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (11) : 3705 - 3707
  • [9] FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES
    AKERMARK, B
    NYSTROM, JE
    REIN, T
    BACKVALL, JE
    HELQUIST, P
    ASLANIAN, R
    TETRAHEDRON LETTERS, 1984, 25 (50) : 5719 - 5722
  • [10] Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes
    Gao, Shang
    Liu, Hao
    Yang, Chi
    Fu, Zhiyuan
    Yao, Hequan
    Lin, Aijun
    ORGANIC LETTERS, 2017, 19 (18) : 4710 - 4713