Functionalization of [2.2]Paracyclophanes via a Reductive Sulfanylation Reaction

被引：7
|
作者：
Deschamps, Damien [1 ]
Lohier, Jean-Francois [1 ]
Richards, Christopher J. [2 ]
Gaumont, Annie-Claude [1 ]
Perrio, Stephane [1 ]
机构：
[1] Normandie Univ, ENSICAEN, UNICAEN, CNRS,LCMT, F-14000 Caen, France
[2] Univ East Anglia, Sch Chem, Norwich NR4 7TJ, Norfolk, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期
关键词：
ORGANOCATALYZED 3+2 ANNULATION; ENANTIOMERICALLY PURE; KINETIC RESOLUTION; LAYERED COMPOUNDS; ALLENYL SULFONES; PARACYCLOPHANES; SULFIDES; PLANAR; EFFICIENT; BRIDGES;
D O I：
10.1021/acs.joc.0c02235
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An expeditious route to planar chiral sulfur-based scaffolds has been achieved in two operational steps from cheap and commercial [2.2]paracyclophane hydrocarbon. The sulfur atom was introduced in a specific benzylic position of the [2.2]paracyclophane according to a reductive sulfanylation reaction, which proceeds under two complementary reaction conditions with either the BF3 center dot OEt2/Et3SiH or TFA/BH3 center dot THF combinations. The study was completed by the development of a highly efficient resolution approach by HPLC.
引用
收藏
页码：507 / 514
页数：8
相关论文
共 50 条
  • [1] [2.2]Paracyclophanes: From Selective Functionalization to Optical Properties
    Wu, Shiqi
    Felder, Simon
    Brom, Jules
    Pointillart, Fabrice
    Maury, Olivier
    Micouin, Laurent
    Benedetti, Erica
    ADVANCED OPTICAL MATERIALS, 2024, 12 (21)
  • [2] Regioselective Functionalization of [2.2]Paracyclophanes: Recent Synthetic Progress and Perspectives
    Hassan, Zahid
    Spuling, Eduard
    Knoll, Daniel M.
    Braese, Stefan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (06) : 2156 - 2170
  • [3] Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement
    Montanari, Matteo
    Bugana, Alberto
    Sharma, Arvind K.
    Pasini, Dario
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5018 - 5020
  • [4] MONOSUBSTITUTED ARYL[2.2]PARACYCLOPHANES
    KUS, P
    POLISH JOURNAL OF CHEMISTRY, 1994, 68 (10) : 1983 - 1988
  • [5] Cycloadditions to alkenyl[2.2]paracyclophanes
    Aly, AA
    Ehrhardt, S
    Hopf, H
    Dix, I
    Jones, PG
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (02) : 335 - 350
  • [6] Orthogonal π-Bridges in [2.2]Paracyclophanes
    Birsa, M. Lucian
    Jones, Peter G.
    Hopf, Henning
    SYNLETT, 2011, (02) : 259 - 261
  • [7] SIMPLE SYNTHESIS OF [2.2]PARACYCLOPHANES
    HOPF, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (05) : 419 - &
  • [8] A NOVEL SYNTHESIS OF[2.2]PARACYCLOPHANES
    BROWN, GW
    SONDHEIM.F
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) : 7116 - &
  • [9] Regioselective Pummerer rearrangement in [2.2]paracyclophanes
    Invernizzi, Fabio
    Nitti, Andrea
    Pasini, Dario
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 196 (02) : 189 - 194
  • [10] STUDIES ON SYNTHESES OF MULTILAYERED [2.2]PARACYCLOPHANES
    OTSUBO, T
    HORITA, H
    MISUMI, S
    SYNTHETIC COMMUNICATIONS, 1976, 6 (08) : 591 - 596
12345