Water soluble phosphines .8. Palladium-catalyzed P-C cross coupling reactions between primary or secondary phosphines and functional aryliodides - A novel synthetic route to water soluble phosphines

被引：186

作者：

Herd, O ^{[1
]}

Hessler, A ^{[1
]}

Hingst, M ^{[1
]}

Tepper, M ^{[1
]}

Stelzer, O ^{[1
]}

机构：

[1] BERG UNIV GESAMTHSCH WUPPERTAL,FACHBEREICH 9,D-42097 WUPPERTAL,GERMANY

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1996年 / 522卷 / 01期

关键词：

P-C cross coupling; tertiary and secondary phosphines; palladium catalysis; water soluble phosphines; bromide; iodide;

D O I：

10.1016/0022-328X(96)06136-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Tertiary phosphines Ph(2)P-Ar and PhP(Ar)(2) containing mono- and disubstituted aromatic ring systems Ar (Ar = C6H4-X and C6H3-XY; X, Y = Me, OH, NH2, COOH, COOMe and SO3Na) are accessible in good yields by Pd(0)-catalyzed cross coupling reactions between diphenylphosphine or phenylphosphine and substituted aryliodides I-C6H4-X or I-C6H3-XY in organic solvents (dimethylacetamide, acetonitrile, methanol) using organic amines or potassium and sodium acetate as bases. If the primary phosphine is employed in the appropriate stoichiometric ratio, functionalized secondary phosphines, e.g. Ph(H)P-C6H4-p-SO3Na, may be obtained selectively.

引用

页码：69 / 76

页数：8

共 11 条

[1] Water-soluble phosphines -: Part XII.: Pd catalyzed P-C coupling reactions:: a novel synthetic route to cationic phosphines with para- and meta-guanidiniumphenyl moieties
Machnitzki, P
Tepper, M
Wenz, K
Stelzer, O
Herdtweck, E
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 602 (1-2) : 158 - 169
[2] Synthesis of secondary phosphines by copper-catalyzed P-C cross-coupling reaction
Frik, Malgorzata
Haber, Aaron
Schiff, Elliot
Camara, James
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[3] Water soluble phosphines - Part XV. Syntheses of multiply functionalized and chiral phosphine ligands by Pd-catalyzed P-C and C-C coupling reactions
Brauer, DJ
Hingst, M
Kottsieper, KW
Liek, C
Nickel, T
Tepper, M
Stelzer, O
Sheldrick, WS
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) : 14 - 26
[4] Copper-catalyzed P-C cross-coupling for the synthesis of secondary phosphines and related ligands.
Frik, Malgorzata
Haber, Aaron
Schiff, Elliot
Camara, James
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[5] P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides
Dai, Qiang
Li, Wenbo
Lo, Zhiming
Zhang, Junliang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (51) : 20556 - 20564
[6] Preparation of Aryl(dicyclohexyl)phosphines by C-P Bond-Forming Cross-Coupling in Water Catalyzed by an Amphiphilic-Resin-Supported Palladium Complex
Hirai, Yoshinori
Uozumi, Yasuhiro
SYNLETT, 2017, 28 (20) : 2966 - 2970
[7] 31P NMR study of a palladium-catalyzed cross-coupling Suzuki reaction using water-soluble TPPTS ligand
Vilaro, Maria
Granell, Jaume
Valencia, Gregorio
Arsequell, Gemma
AFINIDAD, 2007, 64 (528) : 225 - 230
[8] Palladium-catalyzed C-N bond formation: The coupling of challenging substrate combinations, microwave reactions, and development of water-soluble ligands
Anderson, Kevin W.
Tundel, Rachel E.
Ikawa, Takashi
Buchwald, Stephen L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[9] The synthesis of novel directly conjugated zinc(II) phthalocyanine via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction and its quaternized water-soluble derivative: Investigation of photophysical and photochemical properties
Yanik, Hulya
Al-Raqa, Shaya Y.
Aljuhani, Ateyatallah
Durmus, Mahmut
DYES AND PIGMENTS, 2016, 134 : 531 - 540
[10] Water-soluble phosphanes.: 10 -: Novel syntheses of mono- and bisphosphonated aromatic phosphanes by consecutive Pd-catalyzed P-C coupling reactions and nucleophilic phosphanylation -: X-ray structure of Ph2P-C6H4-m-PO3Na2.5.5H2O.iPrOH
Machnitzki, P
Nickel, T
Stelzer, O
Landgrafe, C
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 1998, (07) : 1029 - 1034

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