Conformationally restricted arene intermediates in the intermolecular heck arylation of vinylarenes

被引：12

作者：

Hii, KK

Claridge, TDW

Giernoth, R

Brown, JM

机构：

[1] Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 08期

关键词：

Heck reaction; homogeneous catalysis; NMR spectroscopy; palladium; P ligands; reactive intermediates;

D O I：

10.1002/adsc.200404072

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The NMR observation of o-benzylpalladium intermediates at low temperature, formed by reaction of arylpalladium diphosphine cations with simple vinylarenes, indicates restricted rotation in the adjacent aryl ring. The stability of the intermediate is greater in the dppp than in the dppf series. By a combination of NMR, techniques, it was possible to characterise the intermediate, and to consider permissible structures.

引用

页码：983 / 988

页数：6

共 67 条

[1] Synthesis and characterization of chiral diphosphine platinum(II) VANOL and VAPOL complexes
Becker, JJ
White, PS
Gagné, MR
[J]. ORGANOMETALLICS, 2003, 22 (16) : 3245 - 3249
[2] Böhm VPW, 2001, CHEM-EUR J, V7, P4191
[3] Characterization of reactive intermediates in palladium-catalyzed arylation of methyl acrylate (Heck reaction)
Brown, JM
Hii, KK
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (06): : 657 - 659
[4] STABLE ARYLPALLADIUM IODIDES AND REACTIVE ARYLPALLADIUM TRIFLUOROMETHANESULFONATES IN THE INTRAMOLECULAR HECK REACTION
BROWN, JM
PEREZTORRENTE, JJ
ALCOCK, NW
CLASE, HJ
[J]. ORGANOMETALLICS, 1995, 14 (01) : 207 - 213
[5] Unorthodox C,O binding mode of Me2BINOL in Pt(II) complexes
Brunkan, NM
White, PS
Gagné, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) : 11002 - 11003
[6] NMR structure of an unusual Pt2(μ-BINOL) dimer:: More surprises from a seemingly simple chiral ligand
Brunkan, NM
Gagné, MR
[J]. ORGANOMETALLICS, 2002, 21 (22) : 4711 - 4717
[7] Intramolecular benzylic C-H activation: palladium-catalyzed synthesis of hexahydromethanofluorenes
Catellani, M
Motti, E
Ghelli, S
[J]. CHEMICAL COMMUNICATIONS, 2000, (20) : 2003 - 2004
[8] Catalytic multistep reactions via palladacycles
Catellani, M
[J]. SYNLETT, 2003, (03) : 298 - 313
[9] Palladium-arene interactions in catalytic intermediates:: An experimental and theoretical investigation of the soft rearrangement between η1 and η2 coordination modes
Catellani, M
Mealli, C
Motti, E
Paoli, P
Perez-Carreño, E
Pregosin, PS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) : 4336 - 4346
[10] A novel palladium-catalyzed synthesis of phenanthrenes from ortho-substituted aryl iodides and diphenyl- or alkylphenylacetylenes
Catellani, M
Motti, E
Baratta, S
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3611 - 3614

← 1 2 3 4 5 6 7 →