BrOnsted Acid Catalyzed Intramolecular Allylic Substitution Reaction of Allylic Alcohols: A Facile Synthesis of 2-Vinylchromans

被引:0
|
作者
Li, Yun-Fan [1 ]
Xi, Yu-Ting [1 ]
Hu, Kai-Ji [1 ]
Tan, Qitao [1 ]
Ding, Chang-Hua [1 ]
Xu, Bin [1 ,2 ]
机构
[1] Shanghai Univ, Dept Chem, Shanghai Engn Res Ctr Organ Repair, Innovat Drug Res Ctr, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
BrOnsted acid; allylic substitution reaction; allylic alcohol; chroman; metal-free reactions; ASYMMETRIC-SYNTHESIS; ALKYLATION; CHROMANS; TERTIARY; PHENOLS; CYCLOADDITION; HETEROCYCLES; ALLYLATION; ANNULATION; FLAVONOIDS;
D O I
10.1055/a-2301-9223
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bronsted acid-catalyzed intramolecular allylic substitution reaction of secondary and tertiary allylic alcohols has been developed. A variety of 2-vinylchromans were efficiently prepared in moderate to excellent yields. The given method features wide substrate scope, operational simplicity, metal-free, and mild reaction conditions. The practicability of the method was demonstrated by the gram-scale reaction and further derivations of the product. Catalytic asymmetric reaction was preliminarily studied. © 2024 Georg Thieme Verlag. All rights reserved.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Allylic Substitution Reaction of Benzothiazolylacetamide with Allylic Alcohols in Water
    Pan, Shulei
    Wu, Binqiang
    Hu, Jinjin
    Xu, Ruigang
    Jiang, Min
    Zeng, Xiaofei
    Zhong, Guofu
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (16): : 10111 - 10119
  • [2] Chiral Bronsted Acid-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Indoles with Primary Alcohols
    Zou, Lei-Ming
    Huang, Xian-Yun
    Zheng, Chao
    Cheng, Yuan-Zheng
    You, Shu-Li
    ORGANIC LETTERS, 2022, 24 (19) : 3544 - 3548
  • [3] A Bronsted acid-promoted asymmetric intramolecular allylic amination of alcohols
    Zhou, Jianqiao
    Xie, Hexin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (03) : 380 - 383
  • [4] ALLYLIC ALCOHOLS AS SUBSTRATES FOR THE PALLADIUM(0)-CATALYZED ALLYLIC SUBSTITUTION
    STARY, I
    STARA, IG
    KOCOVSKY, P
    TETRAHEDRON LETTERS, 1993, 34 (01) : 179 - 182
  • [5] FACILE SYNTHESIS OF ALLYLIC ALCOHOLS
    TERAO, S
    SHIRAISHI, M
    KATO, K
    SYNTHESIS-STUTTGART, 1979, (06): : 467 - 468
  • [6] Palladium/Bronsted Acid-Catalyzed α-Allylation of Aldehydes with Allylic Alcohols
    Jiang, Gaoxi
    List, Benjamin
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) : 1667 - 1670
  • [7] FACILE SYNTHESIS OF (E)-ALLYLIC ALCOHOLS BY ACID-CATALYZED MODIFICATION OF THE MISLOW-EVANS REARRANGEMENT OF ALLYLIC SULFOXIDES
    MASAKI, Y
    SAKUMA, K
    KAJI, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (06) : 2531 - 2534
  • [8] Palladium Catalyzed Controllable Mono- or Di-Allylic Substitution Reaction of Benzothiazolylacetate with Allylic Alcohols
    Yan, Peipei
    Pan, Shulei
    Hu, Jinjin
    Lu, Limei
    Zeng, Xiaofei
    Zhong, Guofu
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1322 - 1334
  • [9] Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species
    Sundararaju, Basker
    Achard, Mathieu
    Bruneau, Christian
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (12) : 4467 - 4483
  • [10] Synthesis of Substituted Benzoxacycles via a Pd(II)-Catalyzed Intramolecular Arylation Reaction of Allylic Alcohols
    Li, Jingjie
    Tan, Ceheng
    Mu, Xinpeng
    Gong, Jianxian
    Yang, Zhen
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (05) : 562 - 566