The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols

被引:80
作者
Guo, Songjin [1 ]
Yu, Jin-Tao [1 ]
Dai, Qiang [1 ]
Yang, Haitao [1 ]
Cheng, Jiang [1 ,2 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
[2] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
METAL-FREE; CARBONYL-COMPOUNDS; BUTYL HYDROPEROXIDE; EFFICIENT SYNTHESIS; CARBOXYLIC-ACIDS; ESTERIFICATION; OXIDATION; ALDEHYDES; ESTERS; BENZOYLOXYLATION;
D O I
10.1039/c4cc01652a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Bu4NI-catalyzed reaction of ketones with benzylic alcohols was achieved, leading to alfa-acyloxycarbonyl compounds in moderate to good yields. This metal-free procedure featured the employment of facilely and commercially available starting materials and TBHP as a clean oxidant with high atom economy.
引用
收藏
页码:6240 / 6242
页数:3
相关论文
共 58 条
[1]   Solvent free oxidation of primary alcohols and diols using thymine iron(III) catalyst [J].
Al-Hunaiti, Afnan ;
Niemi, Teemu ;
Sibaouih, Ahlam ;
Pihko, Petri ;
Leskela, Markku ;
Repo, Timo .
CHEMICAL COMMUNICATIONS, 2010, 46 (48) :9250-9252
[2]   2-Hydroxy-1,2,2-triphenylethanone as an efficient photolabile protecting group for carboxylic acids [J].
Ashraf, M. Arfan ;
Russell, Alexander G. ;
Wharton, Christopher W. ;
Snaith, John S. .
TETRAHEDRON, 2007, 63 (03) :586-593
[3]   Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families [J].
Baran, PS ;
Richter, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7450-7451
[4]   A general method for the α-acyloxylation of carbonyl compounds [J].
Beshara, CS ;
Hall, A ;
Jenkins, RL ;
Jones, KL ;
Jones, TC ;
Killeen, NM ;
Taylor, PH ;
Thomas, SP ;
Tomkinson, NCO .
ORGANIC LETTERS, 2005, 7 (25) :5729-5732
[5]   Molecular interactions of new pregnenedione derivatives [J].
Bratoeff, E ;
Ramírez, E ;
Flores, E ;
Valencia, N ;
Sánchez, M ;
Heuze, I ;
Cabeza, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (10) :1132-1136
[6]   Ruthenium(IV)-Catalyzed Markovnikov Addition of Carboxylic Acids to Terminal Alkynes in Aqueous Medium [J].
Cadierno, Victorio ;
Francos, Javier ;
Gimeno, Jose .
ORGANOMETALLICS, 2011, 30 (04) :852-862
[7]   Ruthenium-catalyzed synthesis of β-oxo esters in aqueous medium: Scope and limitations [J].
Cadierno, Victorio ;
Francos, Javier ;
Gimeno, Jose .
GREEN CHEMISTRY, 2010, 12 (01) :135-143
[8]   Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].
Chen, Long ;
Shi, Erbo ;
Liu, Zhaojun ;
Chen, Shulin ;
Wei, Wei ;
Li, Hong ;
Xu, Kai ;
Wan, Xiaobing .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089
[9]   α-Hydroxylation of β-dicarbonyl compounds [J].
Christoffers, J ;
Baro, A ;
Werner, T .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :143-151
[10]   Conversion of Propargylic Alcohols to β-Oxo Esters Catalyzed by Novel Ruthenium-Phosphoramidite Complexes [J].
Costin, Stephen ;
Rath, Nigam P. ;
Bauer, Eike B. .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) :2414-2424