Asymmetric Hydrosilylation of Aromatic Ketones Catalyzed by an Economical and Effective Copper-Diphosphine Catalytic System in Air

被引:8
作者
Liang, Minting [1 ]
Xia, Xiaofeng [1 ]
Liu, Xiang [1 ]
Li, Hexing [2 ]
机构
[1] Jiangnan Univ, Sch Chem & Mat Engn, Minist Educ, Key Lab Food Colloids & Biotechnol, Wuxi 214122, Jiangsu, Peoples R China
[2] Shanghai Normal Univ, Chinese Minist Educ Resource Chem, Key Lab, Shanghai 200234, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; hydrosilylation; ketones; copper salt; polymethylhydrosiloxane; EFFICIENT ENANTIOSELECTIVE HYDROSILYLATION; CONJUGATE REDUCTION; COPPER(II)-DIPYRIDYLPHOSPHINE CATALYST; SELECTIVE HYDROSILYLATION; HETEROARYL KETONES; COMPLEXES; LIGANDS; ARYL; HYDROGENATION; RHODIUM;
D O I
10.1002/cjoc.201500072
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of the inexpensive and non-toxic polymethylhydrosiloxane, the combination of copper(II) acetate and a chiral diphosphine displayed high catalytic efficiency in the asymmetric hydrosilylation of a series of aromatic ketones in air atmosphere and at room temperature. (R)-1-Arylethanols were obtained with up to 99% yield and 93% enantiomeric excess. Meanwhile, the electron effect and steric hindrance of substituents on the aromatic ring had an interesting influence on both the yields and enantioselectivities. Furthermore, a possible mechanism was presented to explain the influence of some key factors on the reaction.
引用
收藏
页码:578 / 582
页数:5
相关论文
共 69 条
[1]   Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones [J].
Addis, Daniele ;
Shaikh, Nadim ;
Zhou, Shaolin ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthius .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) :1687-1691
[2]   Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst [J].
Appella, DH ;
Moritani, Y ;
Shintani, R ;
Ferreira, EM ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9473-9474
[3]   Hydrogen: a good partner for rhodium-catalyzed hydrosilylation [J].
Balan, Cedric ;
Pop, Roxana ;
Comte, Virginie ;
Poinsot, Didier ;
Ratovelomanana-Vidal, Virginie ;
Le Gendre, Pierre .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (07) :517-522
[4]   Bis(oxazoline)titanium complexes as chiral catalysts for enantioselective hydrosilylation of ketones - A combined experimental and theoretical investigation [J].
Bandini, M ;
Bernardi, F ;
Bottoni, A ;
Cozzi, PG ;
Miscione, GP ;
Umani-Ronchi, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) :2972-2984
[5]   [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights [J].
Bette, V ;
Mortreux, A ;
Savoia, D ;
Carpentier, JF .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :289-302
[6]   ASYMMETRICAL CATALYSTS .22. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH CU(1)-CATALYSTS [J].
BRUNNER, H ;
MIEHLING, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 275 (02) :C17-C21
[7]   Selective hydrosilylation of ketones catalyzed by in situ-generated iron NHC complexes [J].
Buitrago, Elina ;
Zani, Lorenzo ;
Adolfsson, Hans .
APPLIED ORGANOMETALLIC CHEMISTRY, 2011, 25 (10) :748-752
[8]  
Cetin A, 2009, CHINESE J CHEM, V27, P978
[9]   Ruthenium catalyzed selective hydrosilylation of aldehydes [J].
Chatterjee, Basujit ;
Gunanathan, Chidambaram .
CHEMICAL COMMUNICATIONS, 2014, 50 (07) :888-890
[10]   Flexible, Bowl-Shaped N-Heterocyclic Carbene Ligands: Substrate Specificity in Iridium-Catalyzed Ketone Hydrosilylation [J].
Chianese, Anthony R. ;
Mo, Allen ;
Datta, Dibyadeep .
ORGANOMETALLICS, 2009, 28 (02) :465-472