Environmentally benign synthesis of H-phosphinic acids using a water-tolerant, recyclable polymer-supported catalyst

被引：59

作者：

Deprèle, S ^{[1
]}

Montchamp, JL ^{[1
]}

机构：

[1] Texas Christian Univ, Dept Chem, Ft Worth, TX 76129 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol0484198

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(GRAPHICS) A reusable polymer-supported hydrophosphinylation catalyst is described for the preparation of H-phosphinic acids. The polystyrene-based ligand is prepared in one step from commercially available compounds. The polymeric catalyst generally gives good yields for a variety of substrates and is water- and air-tolerant, although the scope of alkenes and alkynes which can be employed is somewhat narrower than with our original xantphos/Pd(2)dba(3) Catalyst.

引用

页码：3805 / 3808

页数：4

共 29 条

[1] Generation and fate of regioisomeric side-chain impurities in the preparation of fosinopril sodium [J].

Anderson, NG ;

Coradetti, ML ;

Cronin, JA ;

Davies, ML ;

Gardineer, MB ;

Kotnis, AS ;

Lust, DA ;

Palaniswamy, VA .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (04) :315-319

[2] Recent advances in asymmetric C-C and C-heteroatom bond forming reactions using polymer-bound catalysts [J].

Bräse, S ;

Lauterwasser, F ;

Ziegert, RE .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :869-929

[3] Polymer-supported catalysis in synthetic organic chemistry [J].

Clapham, B ;

Reger, TS ;

Janda, KD .

TETRAHEDRON, 2001, 57 (22) :4637-4662

[4] Palladium-catalyzed hydrophosphinylation of alkenes and alkynes [J].

Deprèle, S ;

Montchamp, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9386-9387

[5] Triethylborane-initiated room temperature radical addition of hypophosphites to olefins:: Synthesis of monosubstituted phosphinic acids and esters [J].

Deprèle, S ;

Montchamp, JL .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6745-6755

[6] THE PHOSPHONOUS ACIDS AND THEIR DERIVATIVES [J].

FRANK, AW .

CHEMICAL REVIEWS, 1961, 61 (04) :389-424

[7]

FRANK AW, 1972, ORGANIC PHOSPHORUS C, V4, pCH10

[8] Wide bite angle diphosphines: Xantphos ligands in transition metal complexes and catalysis [J].

Kamer, PCJ ;

van Leeuwen, PWN ;

Reek, JNH .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (11) :895-904

[9] (PHOSPHINYLOXY)ACYL AMINO-ACID INHIBITORS OF ANGIOTENSIN CONVERTING ENZYME (ACE) .1. DISCOVERY OF (S)-1-[6-AMINO-2-[[HYDROXY(4-PHENYLBUTYL)PHOSPHINYL]OXY]-1-OXOHEXYL]-L-PROLINE, A NOVEL ORALLY ACTIVE INHIBITOR OF ACE [J].

KARANEWSKY, DS ;

BADIA, MC ;

CUSHMAN, DW ;

DEFORREST, JM ;

DEJNEKA, T ;

LOOTS, MJ ;

PERRI, MG ;

PETRILLO, EW ;

POWELL, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :204-212

[10] Synthesis of phosphinic and phosphonic analogs of aspartic acid [J].

Khomutov, AR ;

Osipova, TI ;

Khurs, EN ;

Alferov, KV ;

Khomutov, RM .

RUSSIAN CHEMICAL BULLETIN, 1996, 45 (08) :1961-1964

← 1 2 3 →