Nickel(II) chloride as an efficient and useful catalyst for chemoselective thioacetalization of aldehydes

被引：56

作者：

Khan, AT ^{[1
]}

Mondal, E

Sahu, PR

Islam, S

机构：

[1] Indian Inst Technol, Dept Chem, N Guwahati 781039, Guwahati, India

[2] Dept Chem, Santini Ketan 731235, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 05期

关键词：

protection; dithioacetals; ethanethiol; thiophenol; 1,2-ethanedithiol; 1,3-propanedithiol; nickel(II) chloride;

D O I：

10.1016/S0040-4039(02)02771-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide variety of acyclic and cyclic dithioacetals can be prepared chemoselectively from the corresponding aldehydes by employing a catalytic amount of nickel(II) chloride in dry CH2Cl2-MeOH (5:1) at room temperature in good yields. Some of the major advantages of this procedure are high chemoselectivity, ease of operation, high yields and also compatibility with other protecting groups. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：919 / 922

页数：4

共 44 条

[1] Solvent free thioacetalization of carbonyl compounds catalyzed by Cu(OTf)2-SiO2
Anand, RV
Saravanan, P
Singh, VK
[J]. SYNLETT, 1999, (04) : 415 - 416
[2] AUTENRIETH W, 1899, CHEM BER, V32, P1383
[3] Barua PMB, 2002, SYNLETT, P81
[4] TaCl5-silicagel and TaCl5 as new Lewis acid systems for selective tetrahydropyranylation of alcohols and thioacetalisation, trimerisation and aldolisation of aldehydes.
Chandrasekhar, S
Takhi, M
Reddy, YR
Mohapatra, S
Rao, CR
Reddy, KV
[J]. TETRAHEDRON, 1997, 53 (44) : 14997 - 15004
[5] THIOSILANES, A PROMISING CLASS OF REAGENTS FOR SELECTIVE CARBONYL PROTECTION
EVANS, DA
TRUESDALE, LK
GRIMM, KG
NESBITT, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) : 5009 - 5017
[6] PREPARATION OF ETHYLENETHIOKETALS
FIESER, LF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (07) : 1945 - 1947
[7] Firouzabadi H, 1999, SYNTHESIS-STUTTGART, P58
[8] Firouzabadi H, 1998, SYNLETT, P739
[9] ANHYDROUS LANTHANUM TRICHLORIDE, A MILD AND CONVENIENT REAGENT FOR THIOACETALIZATION
GARLASCHELLI, L
VIDARI, G
[J]. TETRAHEDRON LETTERS, 1990, 31 (40) : 5815 - 5816
[10] Green T. F., 1999, PROTECTIVE GROUPS OR, p[329, 724]

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