A computational study on the acceleration of the Prins reaction by indium trichloride

被引：0

作者：

Drudis-Solé, G ^{[1
]}

Ujaque, G ^{[1
]}

Maseras, F ^{[1
]}

Lledós, A ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Unitat Quim Fis, Bellaterra 08193, Catalonia, Spain

来源：

COMPTES RENDUS CHIMIE | 2004年 / 7卷 / 8-9期

关键词：

DFT method; Prins reaction; indium trichloride; tetrahydropyran;

D O I：

10.1016/j.crci.2004.02.017

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The role of indium trichloride in the Prins reaction, which leads to the formation of a tetrahydropyran ring from an olefin and an aldehyde, is analysed through DFT calculations with the B3LYP functional on a model system defined by 3-buten-1-ol, formaldehyde and indium trichloride. Two different mechanisms are characterized through calculation of all the relevant intermediates and transition states, and one of them is found to be able to explain experimental data, with the higher energy barrier around 25 kcal mol(-1). The reasons why specifically indium trichloride, in contrast to more conventional acids, is particularly efficient in this process, are also analysed. (C) 2004 Academie des sciences. Published by Elsevier SAS. All rights reserved.

引用

页码：885 / 893

页数：9

共 50 条

[31] Indium trichloride-catalyzed conjugate addition of amines to α,β-ethylenic compounds in water
Loh, TP
Wei, LL
SYNLETT, 1998, (09) : 975 - +
[32] Indium Trichloride (InCl3) Catalyzed Synthesis of Fused 7-Azaindole Derivatives Using Domino Knoevenagel-Michael Reaction
Dongare, Sakharam B.
Chavan, Hemant V.
Surwase, Datta N.
Bhale, Pravin S.
Mule, Yoginath B.
Bandgar, Babasaheb P.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2016, 63 (04) : 323 - 330
[33] Bronsted acidic ionic liquids as novel catalysts for Prins reaction
Wang, Wenjuan
Shao, Lili
Cheng, Wenping
Yang, Jiangguo
He, Mingyuan
CATALYSIS COMMUNICATIONS, 2008, 9 (03) : 337 - 341
[34] Indium(III) Triflate-Catalyzed Efficient Prins-Type Cyclization of -Allenols and Aldehydes
Han, Yulin
Tang, Xinjun
Cheng, Jiajia
Ma, Shengming
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (24) : 4019 - 4029
[35] Indium trichloride catalyzed efficient one-pot synthesis of highly substituted furans
Dey, Sumit
Nandi, Debkumar
Pradhan, Prasun K.
Giri, Venkatachalam Sesha
Jaisankar, Parasuraman
TETRAHEDRON LETTERS, 2007, 48 (14) : 2573 - 2575
[36] Bis[(2-diphenylphosphino)phenyl]phenylphosphine as an inflexible tridentate ligand for indium trichloride
Sigl, M
Schier, A
Schmidbaur, H
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1999, 54 (11): : 1417 - 1419
[37] The aza-silyl-prins reaction:: A novel method for the synthesis of Trans-2,6-tetrahydropyridines
Dobbs, AP
Guesné, SJJ
Hursthouse, MB
Coles, SJ
SYNLETT, 2003, (11) : 1740 - 1742
[38] Indium trichloride catalyzed synthesis of 2-aryl-3-aminobenzofuran derivatives by a three-component reaction of phenols, arylglyoxal monohydrates and para-toluenesulfonamide
Chen, CX
Liu, L
Yang, DP
Wang, D
Chen, YJ
SYNLETT, 2005, (13) : 2047 - 2051
[39] On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
Chio, Freda K.
Warne, Julie
Gough, Damien
Penny, Mark
Green , Sasa
Coles, Simon J.
Hursthouse, Mike B.
Jones, Peter
Hassall, Lorraine
McGuire, Thomas M.
Dobbs, Adrian P.
TETRAHEDRON, 2011, 67 (27-28) : 5107 - 5124
[40] First indium trichloride catalyzed self-addition of indoles: One pot synthesis of indolylindolines
Pal, M
Giri, VS
Jaisankar, P
CATALYSIS COMMUNICATIONS, 2005, 6 (11) : 711 - 715

← 1 2 3 4 5 →