High turnover number and rapid, room-temperature amination of chloroarenes using saturated carbene ligands

被引：344

作者：

Stauffer, SR ^{[1
]}

Lee, SW ^{[1
]}

Stambuli, JP ^{[1
]}

Hauck, SI ^{[1
]}

Hartwig, JF ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 10期

关键词：

D O I：

10.1021/ol005751k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A catalytic system for the mild amination of aryl chlorides is described. This system consists of a Pd(0) precursor acid a dihydroimidazoline carbene ligand, which is generated in situ from its protonated tetrafluoroborate salt (2). Using this catalyst, aryl and heteroaryl chlorides react with secondary amines and anilines within hours at room temperature. Turnover numbers as high as 5000 are obtained at elevated temperatures for reaction of morpholine with an unactivated aryl chloride.

引用

页码：1423 / 1426

页数：4

共 30 条

[1] ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES
ARDUENGO, AJ
DIAS, HVR
HARLOW, RL
KLINE, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) : 5530 - 5534
[2] Looking for stable carbenes: The difficulty in starting anew
Arduengo, AJ
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) : 913 - 921
[3] ARDUENGO AJ, Patent No. 5077414
[4] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates
Hamann, BC
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) : 7369 - 7370
[5] Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
[6] 2-L
[7] Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand
Hartwig, JF
Kawatsura, M
Hauck, SI
Shaughnessy, KH
Alcazar-Roman, LM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) : 5575 - 5580
[8] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides
Hartwig, JF
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) : 852 - 860
[9] N-heterocyclic carbenes. 23. High yield syntheses of sterically demanding bis(N-heterocyclic carbene) complexes of palladium
Herrmann, WA
Schwarz, J
Gardiner, MG
[J]. ORGANOMETALLICS, 1999, 18 (20) : 4082 - 4089
[10] N-heterocyclic carbene complexes of palladium and rhodium: cis/trans-isomers
Herrmann, WA
Fischer, J
Ofele, K
Artus, GRJ
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 530 (1-2) : 259 - 262

← 1 2 3 →