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 57 条

[1] EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].

AMATORE, C ;

JUTAND, A ;

MBARKI, MA .

ORGANOMETALLICS, 1992, 11 (09) :3009-3013

[2]

[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23

[3] WATER-SOLUBLE PHOSPHINES AS LIGANDS FOR HYDROFORMYLATION CATALYSTS [J].

BAHRMANN, H ;

BACH, H .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1987, 30 (3-4) :611-614

[4] SYNTHESIS, RESOLUTION AND REACTIONS OF (+/-)-(2-AMINO-PHENYL)METHYLPHENYLPHOSPHINE - CRYSTAL AND MOLECULAR-STRUCTURE OF (R-ASTERISK, R-ASTERISK, S-ASTERISK, R-ASTERISK)-(+/-)-(1,3-BIS([2-(METHYLPHENYL-PHOSPHINO)PHENYL]AMINO)PROPANE)NICKEL(II) PERCHLORATE [J].

BARCLAY, CE ;

DEEBLE, G ;

DOYLE, RJ ;

ELIX, SA ;

SALEM, G ;

JONES, TL ;

WILD, SB ;

WILLIS, AC .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1995, (01) :57-65

[5]

BAUDLER M, 1965, CHEM BER, V104, P1034

[6]

BELETSKAYA IP, 1992, IZV AKAD NAUK K, V7, P1645

[7]

Beller M., 1995, ANGEW CHEM, V107, P1436

[8] WATER-SOLUBLE PHOSPHANES .4. TERTIARY ALKYLPHOSPHANES WITH AMMONIUM GROUPS IN THE SIDE-CHAINS - AMPHIPHILES WITH BASIC P-ATOMS [J].

BITTERER, F ;

KUCKEN, S ;

STELZER, O .

CHEMISCHE BERICHTE, 1995, 128 (03) :275-279

[9]

BITTERER F, UNPUB INORG CHEM

[10] WATER-SOLUBLE PHOSPHANES .3. WATER-SOLUBLE PRIMARY PHOSPHANES WITH AMMONIUM GROUPS NR(2)R' IN THE SIDE-CHAIN - DONOR-FUNCTIONALIZED AMPHIPHILES [J].

BRAUER, DJ ;

FISCHER, J ;

KUCKEN, S ;

LANGHANS, KP ;

STELZER, O ;

WEFERLING, N .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1994, 49 (11) :1511-1524

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