Alkylpalladium N-Heterocyclic Carbene Complexes: Synthesis, Reactivity, and Catalytic Properties

被引：32

作者：

Esposito, Oriana ^{[2
]}

Gois, Pedro M. P. ^{[1
,2
,3
]}

Lewis, Alexandra K. de K. ^{[1
]}

Caddick, Stephen ^{[1
]}

Cloke, F. Geoffrey N. ^{[2
]}

Hitchcock, Peter B. ^{[2
]}

机构：

[1] UCL, Dept Chem, London WC1H OAJ, England

[2] Univ Sussex, Sch Life Sci, Dept Chem & Biochem, Brighton BN1 9QJ, E Sussex, England

[3] Inst Super Tecn, CQFM, Dept Engn Quim & Biol, P-1049001 Lisbon, Portugal

来源：

ORGANOMETALLICS | 2008年 / 27卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/om800455h

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The dimers [trans-[(neopentyl)Pd(mu-Cl)(I(t)lBu)](2), 2, and (cis-[(neopentyl)Pd(mu-Cl)(IPr)](2), 3 ((IBu)-Bu-t = 1,3-bis-tert-butylimidazol-2-ylidene, IPr = 1,3-bis-2,6-diidopropylimidazol-2-ylidene), have been synthesized from [Pd(neopentyl)(Cl)(1,5-COD)], and their reactivity toward a variety of nucleophiles has been evaluated. In particular, this study revealed that 2 can be readily cleaved by primary and secondary amines, affording stable transamination products, which are surprisingly resistant to deprotonation. Dimer 3 was subsequently used as a catalyst in a series of Buchwald-Hartwig amination reactions of aryl chlorides.

引用

页码：6411 / 6418

页数：8

共 62 条

[1] [Anonymous], MODERN AMINATION MET
[2] A STABLE CRYSTALLINE CARBENE
ARDUENGO, AJ
HARLOW, RL
KLINE, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 361 - 363
[3] On the efficiency of two-coordinate palladium(0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides
Arentsen, K
Caddick, S
Cloke, FGN
[J]. TETRAHEDRON, 2005, 61 (41) : 9710 - 9715
[4] Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols
Arentsen, K
Caddick, S
Geoffrey, F
Cloke, N
Herring, AP
Hitchcock, PB
[J]. TETRAHEDRON LETTERS, 2004, 45 (17) : 3511 - 3515
[5] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[6] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
Bellina, F
Carpita, A
Rossi, R
[J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
[7] IODONIUM SALTS FROM ORGANOLITHIUM REAGENTS WITH TRANS-CHLOROVINYLIODOSO DICHLORIDE
BERINGER, FM
NATHAN, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) : 2095 - &
[8] The first example of simple oxidative addition of an aryl chloride to a discrete palladium N-heterocyclic carbene amination precatalyst
Caddick, S
Geoffrey, F
Cloke, N
Hitchcock, PB
Leonard, J
Lewis, AKD
McKerrecher, D
Titcomb, LR
[J]. ORGANOMETALLICS, 2002, 21 (21) : 4318 - 4319
[9] An improved synthesis of bis(1,3-di-N-tert-butylimidazol-2-ylidene)palladium(0) and its use in C-C and C-N coupling reactions
Caddick, S
Cloke, FGN
Clentsmith, GKB
Hitchcock, PB
McKerrecher, D
Titcomb, LR
Williams, MRV
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 635 - 639
[10] Steric and electronic effects in the bonding of N-heterocyclic ligands to transition metals
Cavallo, L
Correa, A
Costabile, C
Jacobsen, H
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) : 5407 - 5413

← 1 2 3 4 5 6 7 →