Palladium-Catalyzed Oxidative Aryltrifluoromethylation of Activated Alkenes at Room Temperature

被引：455

作者：

Mu, Xin ^{[1
]}

Wu, Tao ^{[1
]}

Wang, Hao-yang ^{[2
]}

Guo, Yin-long ^{[2
]}

Liu, Guosheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Mass Spectrometry Ctr, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 02期

关键词：

FORMING REDUCTIVE ELIMINATION; BOND-FORMATION; ARYL IODIDES; C-O; TRIFLUOROMETHYLATION; DIAMINATION; FLUORINE; CONSTRUCTION; OXINDOLES; PD;

D O I：

10.1021/ja210614y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed intramolecular oxidative aryltrifluoromethylation reaction of activated alkenes has been explored. The reaction allows for an efficient synthesis of a variety of CF3-containing oxindoles. Preliminary mechanistic study indicated that the reaction involves a C-sp(3)-Pd-IV(CF3) intermediate, which undergoes reductive elimination to afford a C-sp(3)-CF3 bond.

引用

页码：878 / 881

页数：4

共 73 条

[1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes
Alexanian, EJ
Lee, C
Sorensen, EJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) : 7690 - 7691
[2] Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation
Ball, Nicholas D.
Gary, J. Brannon
Ye, Yingda
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) : 7577 - 7584
[3] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV)
Ball, Nicholas D.
Kampf, Jeff W.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2878 - +
[4] Banks R. E., 1994, ORGANOFLUORINE CHEM
[5] The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles
Chemler, Sherry R.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) : 3009 - 3019
[6] METHYL FLUOROSULFONYLDIFLUOROACETATE - A NEW TRIFLUOROMETHYLATING AGENT
CHEN, QY
WU, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) : 705 - 706
[7] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
Cho, Eun Jin
Senecal, Todd D.
Kinzel, Tom
Zhang, Yong
Watson, Donald A.
Buchwald, Stephen L.
[J]. SCIENCE, 2010, 328 (5986) : 1679 - 1681
[8] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids
Chu, Lingling
Qing, Feng-Ling
[J]. ORGANIC LETTERS, 2010, 12 (21) : 5060 - 5063
[9] Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3
Chu, Lingling
Qing, Feng-Ling
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) : 7262 - +
[10] Cottet F, 2002, EUR J ORG CHEM, V2002, P327

← 1 2 3 4 5 6 7 8 →