(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation

被引：165

作者：

Marion, N

Ecarnot, EC

Navarro, O

Amoroso, D

Bell, A

Nolan, SP ^{[1
]}

机构：

[1] Univ New Orleans, Dept Chem, Dept Chem, New Orleans, LA 70148 USA

[2] Promerus LLC, Brecksville, OH 44141 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 10期

关键词：

n;

D O I：

10.1021/jo060190h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very straightforward synthesis of (IPr) Pd(acac)Cl from two commercially available starting materials, Pd(acac)(2) and IPr center dot HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, ( IPr) Pd( acac) Cl ( 1), has proven to be a highly active Pd-II precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

引用

收藏

页码：3816 / 3821

页数：6

相关论文

共 43 条

[11]

Gribble G W., 2000, Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist

[12]

GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481

[13] Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383

[14] Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].

Hartwig, JF ;

Kawatsura, M ;

Hauck, SI ;

Shaughnessy, KH ;

Alcazar-Roman, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580

[15] Synthesis of 4,5-dianilinophthalimide and related analogues for potential treatment of Alzheimer's disease via palladium-catalyzed amination [J].

Hennessy, EJ ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7371-7375

[16] Structure-based generation of a new class of potent Cdk4 inhibitors:: New de novo design strategy and library design [J].

Honma, T ;

Hayashi, K ;

Aoyama, T ;

Hashimoto, N ;

Machida, T ;

Fukasawa, K ;

Iwama, T ;

Ikeura, C ;

Ikuta, M ;

Suzuki-Takahashi, I ;

Iwasawa, Y ;

Hayama, T ;

Nishimura, S ;

Morishima, H .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (26) :4615-4627

[17] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions [J].

Huang, XH ;

Anderson, KW ;

Zim, D ;

Jiang, L ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6653-6655

[18] Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings [J].

Kataoka, N ;

Shelby, Q ;

Stambuli, JP ;

Hartwig, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5553-5566

[19] Synthesis, complexation and emission behavior of N,N′, N", N"′-tetrakis(1-naphthylmethyl)-1,4,8.11-tetraazacyclotetradecane [J].

Kubo, K ;

Yamamoto, E ;

Sakurai, T .

HETEROCYCLES, 1998, 48 (07) :1477-1481

[20] Reorganization energies in the transports of holes and electrons in organic amines in organic electroluminescence studied by density functional theory [J].

Lin, BC ;

Cheng, CP ;

Lao, ZPM .

JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (26) :5241-5251

← 1 2 3 4 5 →