One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions

被引：61
作者：
Chu, Xue-Qiang [1 ,2 ]
Meng, Hua [1 ,2 ]
Xu, Xiao-Ping [1 ,2 ]
Ji, Shun-Jun [1 ,2 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 32期
基金：
中国国家自然科学基金;
关键词：
iodine; metal-free reactions; multicomponent reactions; sulfur; sulfonylation; EFFICIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE REARRANGEMENTS; AEROBIC DIFUNCTIONALIZATION; SELECTIVE OXIDATION; HYDROGEN-PEROXIDE; ALPHA-ARYLATION; RING EXPANSION; BOND FORMATION; C-S;
D O I：
10.1002/chem.201500469
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A metal-free tandem procedure by using a sulfonylation reaction of aryl allylic alcohols followed by an iodobenzenediacetate (PIDA)-promoted oxidative functionalization has been established. Allylic sulfones, -ketosulfones, and triflyl allylic alcohols have been constructed in a single operation. The methodology incorporates the sulfonyl (both aryl and triflyl) functionality with a simple work-up procedure.
引用
收藏
页码：11359 / 11368
页数：10
相关论文
共 113 条
  • [1] How can the fipronil insecticide access phloem?
    Aajoud, Asmae
    Raveton, Muriel
    Azrou-Isghi, Dalila
    Tissut, Michel
    Ravanel, Patrick
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (10) : 3732 - 3737
  • [2] Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)
    Ahmad, Anees
    Scarassati, Paulo
    Jalalian, Nazli
    Olofsson, Berit
    Silva, Luiz F., Jr.
    [J]. TETRAHEDRON LETTERS, 2013, 54 (43) : 5818 - 5820
  • [3] A Common Building Block for the Syntheses of Amorfrutin and Cajaninstilbene Acid Libraries toward Efficient Binding with Peroxisome Proliferator-Activated Receptors
    Aidhen, Indrapal S.
    Mukkamala, Ramesh
    Weidner, Christopher
    Sauer, Sascha
    [J]. ORGANIC LETTERS, 2015, 17 (02) : 194 - 197
  • [4] Sulfones: new reagents in organocatalysis
    Alba, Andrea-Nekane R.
    Companyo, Xavier
    Rios, Ramon
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) : 2018 - 2033
  • [5] [Anonymous], 2009, ANGEW CHEM-GER EDIT
  • [6] [Anonymous], 2014, ANGEW CHE, DOI DOI 10.1039/C4GC00542B
  • [7] Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide (H2O2) in the presence of zirconium tetrachloride
    Bahrami, K
    [J]. TETRAHEDRON LETTERS, 2006, 47 (12) : 2009 - 2012
  • [8] Micellar Catalysis Using a Photochromic Surfactant: Application to the Pd-Catalyzed Tsuji-Trost Reaction in Water
    Billamboz, Muriel
    Mangin, Floriane
    Drillaud, Nicolas
    Chevrin-Villette, Carole
    Banaszak-Leonard, Estelle
    Len, Christophe
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) : 493 - 500
  • [9] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
    Blakemore, PR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2563 - 2585
  • [10] Mode of action for chloroacetamides and functionally related compounds
    Böger, P
    [J]. JOURNAL OF PESTICIDE SCIENCE, 2003, 28 (03) : 324 - 329
12345678910