Palladium(II)-Catalyzed Conjugate Phosphination of Electron-Deficient Acceptors

被引：30
作者：
Trepohl, Verena T. [1 ]
Mori, Susumu [2 ]
Itami, Kenichiro [2 ]
Oestreich, Martin [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
[2] Nagoya Univ, Grad Sch Sci, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 05期
基金：
日本科学技术振兴机构;
关键词：
ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; SILYL TRANSFER; 1,4-ADDITION; ACIDS; HYDROPHOSPHINATION; SILYLPHOSPHINES; BORATION; ESTERS; 1,4-DIBORATION; LIGANDS;
D O I：
10.1021/ol8028466
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general protocol for the conjugate transfer of diphenyl-, dicyclohexyl-, and di-tert-butylphosphinyl groups from silylphosphlnes to cyclic and acyclic electron-deficient acceptors employing a bench-stable palladium(II) catalyst Is reported. Several E and Z configured alpha,beta-unsaturated carbonyl and carboxyl acceptors (including imides) as well as nitroalkenes participate in this palladium(II)-catalyzed process in high chemical yields.
引用
收藏
页码：1091 / 1094
页数：4
相关论文
共 38 条
  • [1] Platinum catalysed 3,4- and 1,4-diboration of α,β-unsaturated carbonyl compounds using bis-pinacolatodiboron
    Bell, NJ
    Cox, AJ
    Cameron, NR
    Evans, JSO
    Marder, TB
    Duin, MA
    Elsevier, CJ
    Baucherel, X
    Tulloch, AAD
    Tooze, RP
    [J]. CHEMICAL COMMUNICATIONS, 2004, (16) : 1854 - 1855
  • [2] Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis
    Burks, Heather E.
    Morken, James P.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (45) : 4717 - 4725
  • [3] Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes
    Carlone, Armando
    Bartoli, Giuseppe
    Bosco, Marcella
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) : 4504 - 4506
  • [4] Diastereoselective synthesis of α-substituted β-amidophosphonates
    Castelot-Deliencourt, G
    Pannecoucke, X
    Quirion, JC
    [J]. TETRAHEDRON LETTERS, 2001, 42 (06) : 1025 - 1028
  • [5] Addition reactions of phosphorus halides VI The 1,2 and 1,4 addition of diphenyl-chlorophosphine
    Conant, JB
    Braverman, JBS
    Hussey, RE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1923, 45 : 165 - 171
  • [6] ADDITION OF GERMYLPHOSPHINES AND SILYLPHOSPHINES TO ALPHA-ETHYLENIC ALDEHYDES AND KETONES
    COURET, C
    ESCUDIE, J
    SATGE, J
    ANH, NT
    SOUSSAN, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 91 (01) : 11 - 30
  • [7] The phospha-Michael addition in organic synthesis
    Enders, D
    Saint-Dizier, A
    Lannou, MI
    Lenzen, A
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) : 29 - 49
  • [8] Transition metal-catalysed addition reactions of H-heteroatom and inter-heteroatom bonds to carbon-carbon unsaturated linkages via oxidative additions
    Han, LB
    Tanaka, M
    [J]. CHEMICAL COMMUNICATIONS, 1999, (05) : 395 - 402
  • [9] Fluoride-mediated phosphination of alkenes and alkynes by silylphosphines
    Hayashi, M
    Matsuura, Y
    Watanabe, Y
    [J]. TETRAHEDRON LETTERS, 2004, 45 (50) : 9167 - 9169
  • [10] Activation of silylphosphines by diethyl azodicarboxylate: novel silylation of alcohols
    Hayashi, M
    Matsuura, Y
    Watanabe, Y
    [J]. TETRAHEDRON LETTERS, 2004, 45 (07) : 1409 - 1411
1234