Synthesis of Substituted Benzenes via Bi(OTf)3-Mediated Intramolecular Carbonyl Allylation of a-Prenyl or α-Geranyl β-Arylketosulfones

被引：53
作者：
Chang, Meng-Yang [1 ]
Cheng, Yu-Chieh [1 ]
Lu, Yi-Ju [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 80708, Taiwan
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 12期
关键词：
ORGANIC-CHEMISTRY APPLICATION; CROSS-COUPLING REACTIONS; BISMUTH(III) TRIFLATE; REGIOSELECTIVE SYNTHESIS; 2+2+2 CYCLOADDITION; CATALYZED SYNTHESIS; ALLYLIC ALKYLATION; TERTIARY ALCOHOLS; KETO SULFONES; CYCLIZATION;
D O I：
10.1021/acs.orglett.5b01461
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular carbonyl allylation of alpha-prenyl or alpha-geranyl beta-arylketosulfones 5 in the presence of molecule sieves (MS) affords substituted benzenes 6-7 in moderate to good yields. The facile transformation proceeds by a synthetic sequence starting with the alpha-prenylation or alpha-geranylation of 1 and the Bi(OTf)(3)-mediated annulation of 5 followed by a sequential desulfonative aromatization or then an intramolecular FriedelCrafts alkylation. A plausible mechanism has been studied and proposed.
引用
收藏
页码：3142 / 3145
页数：4
相关论文
共 70 条
  • [1] METHODOLOGY TO ESTABLISH 1,2-DIFUNCTIONALITY AND 1,3-DIFUNCTIONALITY FOR THE SYNTHESIS OF CARBOHYDRATE-DERIVATIVES
    AGER, DJ
    EAST, MB
    [J]. TETRAHEDRON, 1992, 48 (14) : 2803 - 2894
  • [2] [Anonymous], SYNTHESIS, DOI DOI 10.1055/S-0029-1216632
  • [3] Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate
    Anzalone, PW
    Baru, AR
    Danielson, EM
    Hayes, PD
    Nguyen, MP
    Panico, AF
    Smith, RC
    Mohan, RS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) : 2091 - 2096
  • [4] Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot 'Mukaiyama-Michael addition/cyclization/ring-contraction' reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes
    Attanas, Orazio A.
    Favi, Gianfranco
    Giorgi, Gianluca
    Mantellini, Fabio
    Karapetyan, Vahuni
    Langer, Peter
    [J]. TETRAHEDRON, 2009, 65 (28) : 5456 - 5461
  • [5] One-Pot Bi(OTf)3-Catalyzed Oxidative Deprotection of tert-Butyldimethyl Silyl Ethers with TEMPO and Co-Oxidants
    Barnych, Bogdan
    Vatele, Jean-Michel
    [J]. SYNLETT, 2011, (14) : 2048 - 2052
  • [6] Bismuth-catalyzed benzylic oxidations with tert-butyl hydroperoxide
    Bonvin, Y
    Callens, E
    Larrosa, I
    Henderson, DA
    Oldham, J
    Burton, AJ
    Barrett, AGM
    [J]. ORGANIC LETTERS, 2005, 7 (21) : 4549 - 4552
  • [7] Applications of bismuth(III) compounds in organic synthesis
    Bothwell, Jason M.
    Krabbe, Scott W.
    Mohan, Ram S.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) : 4649 - 4707
  • [8] Bi(OTf)3-catalysed synthesis of substituted indanes by a double hydroarylation of unactivated 1,3-dienes
    Cacciuttolo, Bastien
    Ondet, Pierrick
    Poulain-Martini, Sophie
    Lemiere, Gilles
    Dunach, Elisabet
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (07): : 765 - 769
  • [9] Access to Polycyclic Derivatives by Triflate-Catalyzed Intramolecular Hydroarylation
    Cacciuttolo, Bastien
    Poulain-Martini, Sophie
    Fontaine-Vive, Fabien
    Abdo, Mahmoud Ali Hussein
    El-Kashef, Hussein
    Dunach, Elisabet
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (33) : 7458 - 7468
  • [10] Efficient Intramolecular Hydroarylation Catalysed by BiIII Triflate
    Cacciuttolo, Bastien
    Poulain-Martini, Sophie
    Dunach, Elisabet
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) : 3710 - 3714
1234567