Dichloromethane activation.: Direct methylenation of ketones and aldehydes with CH2Cl2 promoted by Mg/TiCl4/THF

被引:82
作者
Yan, TH [1 ]
Tsai, CC [1 ]
Chien, CT [1 ]
Cho, CC [1 ]
Huang, PC [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 400, Taiwan
关键词
D O I
10.1021/ol0478887
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This Mg-TiCl4-promoted CH2-transfer reaction of CH2Cl2 represents an extremely simple, practical, and efficient methylenation of a variety of ketones and aldehydes, especially in enolizable or sterically hindered ketones such as 2,2-dimethylcyclohexanone, camphor, and fenchone.
引用
收藏
页码:4961 / 4963
页数:3
相关论文
共 20 条
[1]   RAPID REDUCTION OF SULFONES TO SULFIDES USING LIALH4-TICL4 [J].
AKGUN, E ;
MAHMOOD, K ;
MATHIS, CA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :761-762
[2]   [TI(MGCL)2.XTHF]Q - A REAGENT FOR THE MCMURRY REACTION AND A NOVEL INORGANIC GRIGNARD COMPLEX [J].
ALEANDRI, LE ;
BOGDANOVIC, B ;
GAIDIES, A ;
JONES, DJ ;
LIAO, SJ ;
MICHALOWICZ, A ;
ROZIERE, J ;
SCHOTT, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 459 (1-2) :87-93
[3]   METHYLENATION OF CARBONYL-COMPOUNDS USING CHLOROMETHYL-LITHIUM - A NEW METHOD FOR TERMINAL AND EXOCYCLIC OLEFINS [J].
BARLUENGA, J ;
FERNANDEZSIMON, JL ;
CONCELLON, JM ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (22) :1665-1665
[5]   GEMINAL DIMETALLIC COMPOUNDS - REACTIVITY OF METHYLENE MAGNESIUM HALIDES AND RELATED COMPOUNDS - A GENERAL CARBONYL OLEFINATION REACTION [J].
BERTINI, F ;
GRASSELL.P ;
ZUBIANI, G ;
CAINELLI, G .
TETRAHEDRON, 1970, 26 (05) :1281-&
[6]   THE METHYLENATION OF ENOLIZABLE KETONES AND ESTERS USING ORGANOTITANIUM CHEMISTRY [J].
CLAWSON, L ;
BUCHWALD, SL ;
GRUBBS, RH .
TETRAHEDRON LETTERS, 1984, 25 (50) :5733-5736
[7]   ACTIVATION OF METHYLENETRIPHENYLPHOSPHORANE BY REACTION WITH TERT-BUTYLLITHIUM OR SEC-BUTYLLITHIUM [J].
COREY, EJ ;
KANG, J ;
KYLER, K .
TETRAHEDRON LETTERS, 1985, 26 (05) :555-558
[8]   NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].
COREY, EJ ;
DANHEISER, RL ;
CHANDRASEKARAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265
[9]   ON THE MECHANISM OF THE TITANIUM-INDUCED REDUCTIVE COUPLING OF KETONES TO OLEFINS [J].
DAMS, R ;
MALINOWSKI, M ;
WESTDORP, I ;
GEISE, HY .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) :248-259
[10]   A CERIUM(III) MODIFICATION OF THE PETERSON REACTION - METHYLENATION OF READILY ENOLIZABLE CARBONYL-COMPOUNDS [J].
JOHNSON, CR ;
TAIT, BD .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :281-283