Palladium-Catalyzed Aminocarbonylation of Aryl Halides with 2,4,6-Trichloro-1,3,5-triazine/Formamide Mixed Reagent

被引：14

作者：

Iranpoor, Nasser ^{[1
]}

Panahi, Farhad ^{[1
,2
]}

Roozbin, Fatemeh ^{[1
]}

Erfan, Soodabeh ^{[1
]}

Rahimi, Sajjad ^{[1
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

[2] Amirkabir Univ Technol, Dept Polymer Engn & Color Technol, Tehran, Iran

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 09期

关键词：

Synthetic methods; Palladium; Amides; Amidation; MONOXIDE-FREE AMINOCARBONYLATION; CARBON-MONOXIDE; DIRECT CARBAMOYLATION; CYANURIC CHLORIDE; SITU GENERATION; CARBONYLATION; IODIDES; AMINES; MO(CO)(6); EFFICIENT;

D O I：

10.1002/ejoc.201501607

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this work, the mixture of formamide and 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride or TCT) is introduced as a new amidating agent in Pd-catalyzed aminocarbonylation of aryl halides. In the presence of a catalytic amount of palladium and TCT/formamide reagent, a range of aryl halides (X = Cl, Br, I) were converted into amides efficiently in N, N-dimethylformamide at 120 degrees C.

引用

页码：1781 / 1787

页数：7

共 63 条

[1] Beller M., 2013, TRANSITION METAL CAT
[2] Efficient metal-free hydrositylation of tertiary, secondary and primary amides to amines
Blondiaux, Enguerrand
Cantat, Thibault
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (66) : 9349 - 9352
[3] Aminocarbonylation of Aryl Tosylates to Carboxamides
Chung, Seungwon
Sach, Neal
Choi, Chulho
Yang, Xiaojing
Drozda, Susan E.
Singer, Robert A.
Wright, Stephen W.
[J]. ORGANIC LETTERS, 2015, 17 (11) : 2848 - 2851
[4] BASE-CATALYZED CARBOXYLATION OF ORGANIC HALIDES NICKEL CARBONYL IN PROTIC MEDIA
COREY, EJ
HEGEDUS, LS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (05) : 1233 - &
[5] Palladium-catalyzed conversion of benzylic and allylic halides into α-aryl and β,γ-unsaturated tertiary amides by the use of a carbamoylsilane
Cunico, RF
Pandey, RK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) : 9048 - 9050
[6] Addition of carbamoylsilanes to electrophilically substituted alkenes.: Preparation of β-functionalized tertiary amides
Cunico, RF
Motta, AR
[J]. ORGANIC LETTERS, 2005, 7 (05) : 771 - 774
[7] Direct carbamoylation of alkenyl halides
Cunico, RF
Maity, BC
[J]. ORGANIC LETTERS, 2003, 5 (26) : 4947 - 4949
[8] Direct carbamoylation of aryl halides
Cunico, RF
Maity, MC
[J]. ORGANIC LETTERS, 2002, 4 (24) : 4357 - 4359
[9] An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF
De Luca, L
Giacomelli, G
Porcheddu, A
[J]. ORGANIC LETTERS, 2002, 4 (04) : 553 - 555
[10] Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
Eriksson, Jonas
Aberg, Ola
Langstrom, Bengt
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (03) : 455 - 461

← 1 2 3 4 5 6 7 →