Detritylation procedure under non-acidic conditions: Naphthalene catalysed reductive cleavage of trityl ethers

被引：21
|
作者：
Yus, M [1 ]
Behloul, C [1 ]
Guijarro, D [1 ]
机构：
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 030801, Spain
来源：
SYNTHESIS-STUTTGART | 2003年 / 14期
关键词：
trityl ether; lithium; lithiation; detritylation; reductive cleavage;
D O I：
10.1055/s-2003-41057
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of primary, secondary, allylic and benzylic trityl ethers 1 with lithium powder and a catalytic amount of naphthalene led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols 2 in good to excellent yields under very mild reaction conditions. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalised trityl ethers. This methodology represents a new and efficient detritylation procedure under non-acidic reaction conditions.
引用
收藏
页码：2179 / 2184
页数：6
相关论文
共 32 条
  • [21] HETEROAROMATIC BORON-COMPOUNDS .11. NITRATION OF 3,2-BORAZAROPYRIDINES UNDER NON-ACIDIC CONDITIONS
    GRONOWITZ, S
    MALTESSON, A
    ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (04): : 457 - 460
  • [22] A catalytic aldol reaction between ketene silyl acetals and aldehydes promoted by lithium amide under non-acidic conditions
    Fujisawa, H
    Mukaiyama, T
    CHEMISTRY LETTERS, 2002, (02) : 182 - 183
  • [23] HETEROAROMATIC BORON-COMPOUNDS .12. HALOGENATION OF 3,2-BORAZAROPYRIDINES UNDER NON-ACIDIC CONDITIONS
    GRONOWITZ, S
    MALTESSON, A
    ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (04): : 461 - 467
  • [24] A CONVENIENT SYNTHESIS OF SUBSTITUTED QUINOLINES BY THERMAL OR PHOTOCHEMICAL ELECTROCYCLIC REARRANGEMENT OF ORTHO-VINYL IMIDATES UNDER NON-ACIDIC CONDITIONS
    QIANG, LG
    BAINE, NH
    TETRAHEDRON LETTERS, 1988, 29 (29) : 3517 - 3520
  • [25] Unique textural properties of titanium-doped alumina via sol-gel synthesis under non-acidic conditions
    Khaleel, Abbas
    Shehadi, Ihsan
    Al-Marzouqi, Ali
    MATERIALS LETTERS, 2012, 68 : 11 - 13
  • [26] TRANSFORMATION OF CARBOXYLIC-ACID TERT-BUTYL ESTERS INTO THE CORRESPONDING TRIMETHYLSILYL ESTERS OR FREE ACIDS UNDER NON-ACIDIC CONDITIONS
    BORGULYA, J
    BERNAUER, K
    SYNTHESIS-STUTTGART, 1980, (07): : 545 - 547
  • [27] A NOVEL ROUTE TO QUINOLINE DERIVATIVES FROM 1,3-PROPANEDIOL AND AMINOARENES - RUTHENIUM CATALYZED HETEROCYCLIZATION UNDER NON-ACIDIC CONDITIONS
    TSUJI, Y
    NISHIMURA, H
    HUH, KT
    WATANABE, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (03) : C44 - C46
  • [28] Zeofen: A user-friendly catalyst for oxidative cleavage of tetrahydropyranyl ethers under non-aqueous conditions
    Mohajerani, B
    Heravi, MM
    Ajami, D
    MONATSHEFTE FUR CHEMIE, 2001, 132 (07): : 871 - 873
  • [29] Zeofen: A User-Friendly Catalyst for Oxidative Cleavage of Tetrahydropyranyl Ethers Under Non-Aqueous Conditions
    Bagher Mohajerani
    Majid M. Heravi
    Dariush Ajami
    Monatshefte für Chemie / Chemical Monthly, 2001, 132 : 871 - 873
  • [30] Pd(TFA)2-catalyzed oxidative coupling of anilides with olefins through C-H bond activation under non-acidic conditions
    Yu, Xiaoli
    Yao, Wei
    Wan, Huida
    Xu, Zhaojun
    Wang, Dawei
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 822 : 100 - 103
1234