Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols

被引：86

作者：

Kananovich, Dzmitry G. ^{[1
]}

Konik, Yulia A. ^{[2
]}

Zubrytski, Dzmitry M. ^{[2
]}

Jaerving, Ivar ^{[1
]}

Lopp, Margus ^{[1
]}

机构：

[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia

[2] Belarusian State Univ, Dept Organ Chem, Minsk 220050, BELARUS

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 39期

关键词：

CONJUGATE ADDITION; TERMINAL ALKYNES; BOND FORMATION; FRAGMENTATION; ARYLATION; OXIDATION; ALCOHOLS; SYSTEM; ETHERS; ALPHA;

D O I：

10.1039/c5cc02386f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tertiary cyclopropanols react rapidly with Togni reagent in methanol at room temperature in the presence of catalytic amounts (3 mol%) of CuCl affording beta-trifluoromethyl ketones in 65-73% isolated yields. Ring opening in 1,2-dialkylsubstituted cyclopropanols gives a mixture of isomeric beta-trifluoromethyl ketones in about 50% combined yield.

引用

页码：8349 / 8352

页数：4

共 50 条

[31] Synthesis of β-alkoxy-N-protected phenethylamines via one-pot copper-catalyzed aziridination and ring opening
Saavedra-Olavarria, Jorge
Madrid-Rojas, Matias
Almodovar, Iriux
Hermosilla-Ibanez, Patricio
Perez, Edwin G.
RSC ADVANCES, 2018, 8 (49): : 27919 - 27923
[32] Highly Regio- and Stereoselective Synthesis of Boron-Substituted Enynes via Copper-Catalyzed Borylation of Conjugated Diynes
Li, DingXi
Kim, Yeong Eun
Yun, Jaesook
ORGANIC LETTERS, 2015, 17 (04) : 860 - 863
[33] Copper-catalyzed synthesis of α,β-unsaturated acylamides via direct amidation from cinnamic acids and N-substituted formamides
Yan, Hong
Yang, Hailong
Lu, Linhua
Liu, Defu
Rong, Guangwei
Mao, Jincheng
TETRAHEDRON, 2013, 69 (35) : 7258 - 7263
[34] Chemodivergent synthesis of multi-substituted/fused pyrroles via copper-catalyzed carbene cascade reaction of propargyl α-iminodiazoacetates
Zhang, Cheng
Chang, Sailan
Qiu, Lihua
Xu, Xinfang
CHEMICAL COMMUNICATIONS, 2016, 52 (84) : 12470 - 12473
[35] Copper-catalyzed oxidative direct C3-cyanoarylation of quinoxalin-2(1H)-ones via denitrogenative ring-opening of 3-aminoindazoles
Mou, Chen-Xu
Yuan, Jin-Wei
Hu, Qian
Han, Bing-Jie
Yang, Liang-Ru
Xiao, Yong-Mei
Fan, Lu-Lu
Zhang, Shou-Ren
Qu, Ling-Bo
NEW JOURNAL OF CHEMISTRY, 2023, 47 (08) : 3783 - 3792
[36] Copper-Catalyzed Ring Expansion of Cyclopropyl Ketones/Formation of N-acyliminium/Hetero-[4+2]-Cycloaddition: A Route to Substituted Pentacyclic Isoindolin-1-one
Li, Jian
Bai, Shuhua
Li, Yang
Wang, Zhengbing
Huo, Xiaoyu
Liu, Li
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) : 8780 - 8785
[37] One-pot synthesis of substituted indolines via a copper-catalyzed sequential multicomponent/C-N coupling reaction
Jin, Hongwei
Zhou, Bingwei
Wu, Zhi
Shen, Yang
Wang, Yanguang
TETRAHEDRON, 2011, 67 (06) : 1178 - 1182
[38] Access to Stereodefined Multifunctionalized β,γ-Unsaturated Ketones via Chemo-, Regio- and Diastereoselective Copper-Catalyzed Diborylation of Cross-Conjugated Enynones†
Zhang, Shuai
Duan, Xinhua
Li, Pengfei
CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (03) : 590 - 596
[39] Copper-catalyzed [3+2] annulation of ethynyl epoxides with malononitrile to access highly substituted dihydrofurans with an all-carbon quaternary stereocenter
Li, Xuanyi
Han, Chunhua
Huang, Yue
Yao, Hequan
Lin, Aijun
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (02) : 245 - 248
[40] Copper-Catalyzed Three-Component Tandem Reaction of Alkynes, α-Diazo Esters, and TMSN3 to Access N-Substituted 1,2,3-Triazoles
Lv, Yufen
Wang, Zhiwei
Song, Lianhui
Hao, Jindong
Zhu, Shuyun
Yue, Huilan
Wei, Wei
Yi, Dong
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24) : 17266 - 17273

← 1 2 3 4 5 →