Selective hydroformylation-acetalization of various olefins using simple and efficient Rh-phosphinite complex catalyst

被引:21
作者
Khan, Shoeb R. [1 ]
Bhanage, Bhalchandra M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India
关键词
Hydroformylation; Acetalization; Aldehydes; Acetals; Rh-phosphinite complex; ASYMMETRIC HYDROFORMYLATION; RHODIUM; DIPHOSPHINITE; ALKENES; ACETALS;
D O I
10.1016/j.tetlet.2013.08.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient Rh-phosphinite complex catalyst was studied for the selective hydroformylation of various olefins. The influence of various reaction parameters including the effect of temperature, pressure, catalyst loading, time, and solvents was studied. The protocol was also applied for the synthesis of various acetals via tandem hydroformylation-acetalization of olefins in alcohols as solvents. High activity and selectivity for acetal formation was achieved in the absence of co-catalysts with admirable substrate to catalyst mole ratio (TON 2500). The developed protocol works for a wide range of olefins to synthesize corresponding aldehydes and acetals under optimized reaction conditions. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5998 / 6001
页数:4
相关论文
共 29 条
[1]   CHELATING DIPHOSPHITE COMPLEXES OF NICKEL(0) AND PLATINUM(0) - THEIR REMARKABLE STABILITY AND HYDROCYANATION ACTIVITY [J].
BAKER, MJ ;
HARRISON, KN ;
ORPEN, AG ;
PRINGLE, PG ;
SHAW, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (12) :803-804
[2]   Synthesis and transition metal chemistry of a bridging diphosphinite, 1,4 bis(diphenylphosphinoxy)benzene [J].
Balakrishna, Maravanji S. ;
Suresh, D. ;
Kumar, Pawan ;
Mague, Joel T. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (23) :3616-3622
[3]   Hydroformylation of styrene catalyzed by a rhodium thiolate binuclear catalyst supported on a cationic exchange resin [J].
Balué, J ;
Bayón, JC .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 137 (1-3) :193-203
[4]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[5]   HYDRIDORHODIUM DIPHOSPHITE CATALYSTS IN THE ASYMMETRIC HYDROFORMYLATION OF STYRENE [J].
BUISMAN, GJH ;
VOS, EJ ;
KAMER, PCJ ;
VANLEEUWEN, PWNM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (03) :409-417
[6]   Synthesis of Fragrance Compounds from Biorenewables: Tandem Hydroformylation-Acetalization of Bicyclic Monoterpenes [J].
de Freitas, Marina C. ;
Vieira, Camila G. ;
dos Santos, Eduardo N. ;
Gusevskaya, Elena V. .
CHEMCATCHEM, 2013, 5 (07) :1884-1890
[7]   Formation of Acetals under Rhodium-Catalyzed Hydroformylation Conditions in Alcohols [J].
Diebolt, Olivier ;
Cruzeuil, Clement ;
Muller, Christian ;
Vogt, Dieter .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (04) :670-677
[8]   Novel diphosphite derived from d-gluco-furanose provides high regio- and enantioselectivity in Rh-catalysed hydroformylation of vinyl arenes [J].
Diéguez, M ;
Pàmies, O ;
Ruiz, A ;
Castillón, S ;
Claver, C .
CHEMICAL COMMUNICATIONS, 2000, (17) :1607-1608
[9]   Hydroformylation of 1-hexene using Rh/TPPTS complex exchanged on anion exchange resin: kinetic studies [J].
Diwakar, MM ;
Deshpande, RM ;
Chaudhari, RV .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 232 (1-2) :179-186
[10]   Tandem reaction sequences under hydroformylation conditions:: New synthetic applications of transition metal catalysis [J].
Eilbracht, P ;
Bärfacker, L ;
Buss, C ;
Hollmann, C ;
Kitsos-Rzychon, BE ;
Kranemann, CL ;
Rische, T ;
Roggenbuck, R ;
Schmidt, A .
CHEMICAL REVIEWS, 1999, 99 (11) :3329-3365