Nickel-catalyzed addition of P(O)-H bonds to propargyl alcohols: One-pot generation of phosphinoyl 1,3-butadienes

被引：54

作者：

Han, LB ^{[1
]}

Ono, Y ^{[1
]}

Yazawa, H ^{[1
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 14期

关键词：

D O I：

10.1021/ol0508431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diphenylphosphine oxide and related P(O)H compounds react with propargyl alcohols at room temperature in the presence of a catalytic amount of Ni(O) complex and Ph2P(O)OH to produce high yields of phosphinoyl 1,3-dienes though an efficient in situ dehydration process.

引用

页码：2909 / 2911

页数：3

共 26 条

[1] FACILE ROUTE TO 1-PHOSPHORYL-1,3-DIENES AND 1-SULFONYL-1,3-DIENES VIA PALLADIUM-CATALYZED ELIMINATION OF ALLYLIC ACETATES [J].

AKERMARK, B ;

NYSTROM, JE ;

REIN, T ;

BACKVALL, JE ;

HELQUIST, P ;

ASLANIAN, R .

TETRAHEDRON LETTERS, 1984, 25 (50) :5719-5722

[2]

BREL VK, 1989, J GEN CHEM USSR ENGL, V59, P2142

[3]

Darcel C, 1996, SYNTHESIS-STUTTGART, P711

[4] CYCLOADDITION REACTIONS OF ENAMINES AND DIETHYL 1,3-BUTADIENEPHOSPHONATE - FORMATION OF BETA-AMINOPHOSPHONATES VIA A MANNICH REACTION [J].

DARLING, SD ;

SUBRAMANIAN, N .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (19) :2851-2852

[5]

DARLING SD, 1979, TETRAHEDRON LETT, V30, P2761

[6]

DARLING SD, 1979, TETRAHEDRON LETT, V30, P2757

[7]

Edmundson R. S., 1996, CHEM ORGANOPHOSPHORU, V4, P495

[8] PHOSPHONIC ACIDS AND ESTERS .21. DIMERIZATION AND DIELS-ALDER REACTIONS OF DIALKYL 1-(1,3-BUTADIENYL)PHOSPHONATES [J].

GRIFFIN, CE ;

DANIEWSK.WM .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) :1691-&

[9] Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes [J].

Han, LB ;

Zhang, C ;

Yazawa, H ;

Shimada, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5080-5081

[10] Retention of configuration on the oxidative addition of P-H bond to platinum (0) complexes: The first straightforward synthesis of enantiomerically pure P-chiral alkenylphosphinates via palladium-catalyzed stereospecific hydrophosphinylation of alkynes [J].

Han, LB ;

Zhao, CQ ;

Onozawa, SY ;

Goto, M ;

Tanaka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (15) :3842-3843

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