Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions

被引：15

作者：

Yin, Guodong ^{[1
]}

Gao, Meng ^{[1
]}

Wang, Zihua ^{[1
]}

Wu, Yandong ^{[2
]}

Wu, Anxin ^{[1
]}

机构：

[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

[2] Xiangtan Univ, Coll Chem, Xiangtan 411105, Peoples R China

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2008年 / 81卷 / 03期

关键词：

D O I：

10.1246/bcsj.81.369

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aromatic methyl ketones, P-keto esters, and trifluoromethyl-1,3-diketones can be directly converted to arenecarboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.

引用

页码：369 / 372

页数：4

共 50 条

[1] CARBON-CARBON BOND-CLEAVAGE REACTIONS IN DECOMPOSITION OF METALLACYCLES
GRUBBS, RH
MIYASHITA, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (23) : 7418 - 7420
[2] CATION PHOTOGENERATION VIA CARBON-CARBON BOND-CLEAVAGE
ROST, JM
CLIFTON, MF
BOYD, MK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 218 - ORGN
[3] NOVEL CARBON-CARBON BOND-CLEAVAGE REACTIONS OF ALPHA-AZOHYDROPEROXIDES
UTAKA, M
FUJITA, Y
TAKEDA, A
CHEMISTRY LETTERS, 1982, (10) : 1607 - 1610
[4] CARBON-CARBON BOND-CLEAVAGE BY THE HALLER-BAUER AND RELATED REACTIONS - A REVIEW
GILDAY, JP
PAQUETTE, LA
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (02) : 167 - &
[5] CARBON-CARBON BOND-CLEAVAGE IN THE COURSE OF A WITTIG REACTION
KOPECKY, J
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 31 - ORGN
[6] OXIDATIVE SECO REARRANGEMENT - A NOVEL CARBON-CARBON BOND-CLEAVAGE
TROST, BM
HIROI, K
JUNGHEIM, LN
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10): : 1839 - 1847
[7] CARBON-CARBON BOND-CLEAVAGE IN PHOTOGENERATED RADICAL-ANIONS
MASLAK, P
KULA, J
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1991, 194 : 293 - 304
[8] Oxidative aliphatic carbon-carbon bond cleavage reactions
Allpress, Caleb J.
Berreau, Lisa M.
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) : 3005 - 3029
[9] Aromatic Cations from Oxidative Carbon-Hydrogen Bond Cleavage in Bimolecular Carbon-Carbon Bond Forming Reactions
Clausen, Dane J.
Floreancig, Paul E.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15): : 6574 - 6582
[10] Selective intermolecular coupling of alkynes with nitriles and ketones via β,β′ carbon-carbon bond cleavage of zirconacyclopentenes
Takahashi, T
Xi, CJ
Xi, ZF
Kageyama, M
Fischer, R
Nakajima, K
Negishi, E
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20): : 6802 - 6806

← 1 2 3 4 5 →