Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols

被引:47
作者
Bravo-Altamirano, Karla [1 ]
Montchamp, Jean-Luc [1 ]
机构
[1] Texas Christian Univ, Dept Chem, Ft Worth, TX 76129 USA
关键词
D O I
10.1021/ol061828e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel palladium-catalyzed allylation of H3PO2 with allylic alcohols is described. The phosphorus-carbon bond-forming reaction produces allylic-H-phosphinic acids and water, in the absence of additives. Primary H-phosphinic acids are obtained in excellent yields, whereas secondary H-phosphinic acids react sluggishly. A reusable polymer-supported catalyst is also described. The reaction provides an environmentally sound approach to H-phosphinic acids.
引用
收藏
页码:4169 / 4171
页数:3
相关论文
共 40 条
[1]   Direct monoalkylation of alkyl phosphinates to access H-phosphinic acid esters [J].
Abrunhosa-Thomas, I ;
Ribière, P ;
Adcock, AC ;
Montchamp, JL .
SYNTHESIS-STUTTGART, 2006, (02) :325-331
[2]   1,1-Diethoxyethylphosphinates and phosphonites. Intermediates for the synthesis of functional phosphorus acids [J].
Baylis, EK .
TETRAHEDRON LETTERS, 1995, 36 (51) :9385-9388
[3]  
BELAKHOV VV, 1983, J GEN CHEM USSR, V53, P1345
[4]   SYNTHESIS OF ALKYL PHOSPHINIC ACIDS FROM SILYL PHOSPHONITES AND ALKYL-HALIDES [J].
BOYD, EA ;
REGAN, AC ;
JAMES, K .
TETRAHEDRON LETTERS, 1994, 35 (24) :4223-4226
[5]   Palladium-catalyzed phosphorus-carbon bond formation: cross-coupling reactions of alkyl phosphinates with aryl, heteroaryl, alkenyl, benzylic, and allylic halides and triflates [J].
Bravo-Altamirano, K ;
Huang, ZH ;
Montchamp, JL .
TETRAHEDRON, 2005, 61 (26) :6315-6329
[6]  
BRAVOALTAMIRANO K, 2006, 231 NAT M AM CHEM SO
[7]   A highly efficient and practical synthesis of cyclic phosphinates using ring-closing metathesis [J].
Bujard, M ;
Gouverneur, V ;
Mioskowski, C .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :2119-2123
[8]   Palladium-triethylborane-triggered direct and regioselective conversion of allylic alcohols to allyl phenyl sulfones [J].
Chandrasekhar, S ;
Jagadeshwar, V ;
Saritha, B ;
Narsihmulu, C .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6506-6507
[9]   Environmentally benign synthesis of H-phosphinic acids using a water-tolerant, recyclable polymer-supported catalyst [J].
Deprèle, S ;
Montchamp, JL .
ORGANIC LETTERS, 2004, 6 (21) :3805-3808
[10]   A novel and convenient preparation of hypophosphite esters [J].
Deprèle, S ;
Montchamp, JL .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 643 :154-163