Fe/Cu-Mediated One-Pot Ketone Synthesis

被引:17
作者
Kumar, Vemula Praveen [1 ]
Babu, Vaddela Sudheer [1 ]
Yahata, Kenzo [1 ]
Kishi, Yoshito [1 ]
机构
[1] Harvard Univ, Dept Chem & Chem Biol, 12 Oxford St, Cambridge, MA 02138 USA
关键词
GRIGNARD-REAGENTS; ALKYL-HALIDES; COMPLEXES; CHLORIDES; ESTERS; ROUTE; ACIDS;
D O I
10.1021/acs.orglett.7b01128
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An Fe/Cu-mediated one-pot ketone synthesis was reported; Unlike Ni- and Pd-mediated one-pot ketone syntheses, the reported Fe/Cu-mediated method allowed selective activation and coupling of alkyl iodides over vinyl iodides. The newly developed one-pot ketone synthesis was applied to a synthesis of vinyl iodide/ketone 13, the left half of halichondrin B, as well as vinyl iodide/ketone 8a, the C20-C26 building block of halichondrins.
引用
收藏
页码:2766 / 2769
页数:4
相关论文
共 29 条
[1]  
Ai Y., UNPUB
[2]   CONVENIENT METHOD FOR PREPARATION OF KETONES BY REACTION OF GRIGNARD-REAGENTS WITH CARBOXYLIC-ACID DERIVATIVES [J].
ARAKI, M ;
SAKATA, S ;
TAKEI, H ;
MUKAIYAM.T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1974, 47 (07) :1777-1780
[3]   Synthesis of iron(II), manganese(II), cobalt(II) and ruthenium(II) complexes containing tridentate nitrogen ligands and their application in the catalytic oxidation of alkanes [J].
Britovsek, GJP ;
England, J ;
Spitzmesser, SK ;
White, AJP ;
Williams, DJ .
DALTON TRANSACTIONS, 2005, (05) :945-955
[4]   SYNTHETIC STUDIES TOWARDS HALICHONDRINS - SYNTHESIS OF THE LEFT HALF OF HALICHONDRINS [J].
BUSZEK, KR ;
FANG, FG ;
FORSYTH, CJ ;
JUNG, SH ;
KISHI, Y ;
SCOLA, PM ;
YOON, SK .
TETRAHEDRON LETTERS, 1992, 33 (12) :1553-1556
[5]   A HIGHLY EFFICIENT SYNTHETIC ROUTE TO KETONES THROUGH SEQUENTIAL COUPLING REACTIONS OF GRIGNARD-REAGENTS WITH S-PHENYL CARBONOCHLORIDOTHIOATE IN THE PRESENCE OF NICKEL OR IRON CATALYSTS [J].
CARDELLICCHIO, C ;
VIANDANESE, V ;
MARCHESE, G ;
RONZINI, L .
TETRAHEDRON LETTERS, 1985, 26 (30) :3595-3598
[6]   Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445
[7]   Reaction of acyl chlorides with organometallic reagents: A banquet table of metals for ketone synthesis [J].
Dieter, RK .
TETRAHEDRON, 1999, 55 (14) :4177-4236
[8]   New Syntheses of E7389 C14-C35 and Halichondrin C14-C38 Building Blocks: Reductive Cyclization and Oxy-Michael Cyclization Approaches [J].
Dong, Cheng-Guo ;
Henderson, James A. ;
Kaburagi, Yosuke ;
Sasaki, Takeo ;
Kim, Dae-Shik ;
Kim, Joseph T. ;
Urabe, Daisuke ;
Guo, Haibing ;
Kishi, Yoshito .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) :15642-15646
[9]   ONE-STEP SYNTHESIS OF KETONES FROM CARBOXYLIC-ACIDS AND GRIGNARD-REAGENTS IN THE PRESENCE OF A NICKEL(II)-PHOSPHINE CATALYST [J].
FIANDANESE, V ;
MARCHESE, G ;
RONZINI, L .
TETRAHEDRON LETTERS, 1983, 24 (34) :3677-3680
[10]   Kumada-Tamao-Corriu Coupling of Alkyl Halides Catalyzed by an Iron-Bisphosphine Complex [J].
Hatakeyama, Takuji ;
Fujiwara, Yu-ichi ;
Okada, Yoshihiro ;
Itoh, Takuma ;
Hashimoto, Toru ;
Kawamura, Shintaro ;
Ogata, Kazuki ;
Takaya, Hikaru ;
Nakamura, Masaharu .
CHEMISTRY LETTERS, 2011, 40 (09) :1030-1032