Recent Advances in the Direct Nucleophilic Substitution of Allylic Alcohols through SN1-Type Reactions

被引:91
|
作者
Baeza, Alejandro [1 ]
Najera, Carmen
机构
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 01期
关键词
S(N)1 reaction; allylic substitution; carbocations; allylic alcohols; green chemistry; PI-ACTIVATED ALCOHOLS; CATALYZED DIRECT SUBSTITUTION; FRIEDEL-CRAFTS ALKYLATION; BETA-DICARBONYL COMPOUNDS; C BOND FORMATION; HYDROXY GROUP; FLUORINATED ALCOHOLS; 1,3-DICARBONYL COMPOUNDS; HETEROATOM NUCLEOPHILES; HOMOGENEOUS CATALYSIS;
D O I
10.1055/s-0033-1340316
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct nucleophilic substitution reactions of allylic alcohols are environmentally friendly, since they generate only water as a byproduct, allowing access to new allylic compounds. This reaction has, thus, attracted the interest of the chemical community and several strategies have been developed for its successful accomplishment. This review gathers the latest advances in this methodology involving S(N)1-type reactions. 1Introduction 2S(N)1-Type Direct Nucleophilic Substitution Reactions of Allylic Alcohols 2.1Lewis Acids as Catalysts 2.2BrOnsted Acids as Catalysts 2.3Other Promoters 3Conclusions and Outlook
引用
收藏
页码:25 / 34
页数:10
相关论文
共 50 条
  • [41] ION-MOLECULE REACTIONS IN THE GAS-PHASE .1. STEREOSPECIFIC NUCLEOPHILIC-SUBSTITUTION OF TERTIARY ALCOHOLS BY AMMONIA
    BASTARD, J
    MANH, DDK
    FETIZON, M
    TABET, JC
    FRAISSE, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (12): : 1591 - 1595
  • [42] REACTIONS OF 2,2,2-TRIPHENYLETHYL PARA-TOLUENESULFONATE IN ALCOHOL SOLUTIONS IN PRESENCE OF BASE UNDER HIGH-PRESSURE - EFFECTS OF PRESSURE ON SN1-TYPE AND SN2-TYPE REACTIONS
    LEE, KI
    OKAMOTO, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09): : 1552 - 1555
  • [43] Et3B-mediated palladium-catalyzed direct allylic substitution reactions of Morita-Baylis-Hillman alcohols with aromatic amines
    Abidi, Ahlem
    Oueslati, Yosra
    Rezgui, Farhat
    [J]. SYNTHETIC COMMUNICATIONS, 2016, 46 (23) : 1916 - 1923
  • [44] CORRELATION OF RATE CONSTANTS OF TYPE SN2 SUBSTITUTION-REACTIONS THROUGH IONIZATION-POTENTIALS
    GUBAIDULLIN, MG
    [J]. ZHURNAL OBSHCHEI KHIMII, 1982, 52 (04): : 939 - 941
  • [45] Iron(III) chloride-catalysed direct nucleophilic α-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols
    Zhang, Xiaoxiang
    Rao, Weidong
    Chan, Sally Wai Hong
    Chan, Philip Wai Hong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (20) : 4186 - 4193
  • [46] 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) Promoted N-Alkylation of Quinazolinones through Nucleophilic Substitution of Benzyl Alcohols
    Zhang, Zhiguang
    Zhang, Xiaomin
    Liu, Yanmei
    Wang, Xu
    Zhang, Xiaolei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 14189 - 14192
  • [48] Metal-Free Direct Aryltrifluoromethylation of Allylic Alcohols with Langlois' Reagent through Concomitant 1,2-Aryl Migration
    Huang, Hong-Li
    Yan, Hang
    Gao, Guo-Lin
    Yang, Chao
    Xia, Wujiong
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (07) : 674 - 677
  • [49] Recent advances in treatment of youth with Type 1 diabetes: better care through technology
    Tamborlane, WV
    Bonfig, W
    Boland, E
    [J]. DIABETIC MEDICINE, 2001, 18 (11) : 864 - 870
  • [50] Recent advances in the substitution reactions of thriorganylstannyl ions with aromatic compounds by the SRN1 mechanism.: Synthetic applications
    Córsico, EF
    Postigo, A
    Rossi, RA
    [J]. MOLECULES, 2000, 5 (09): : 1068 - 1079