Palladium(II)-catalyzed conjugate addition of arylsiloxanes in water

被引：47

作者：

Lerebours, Rachel ^{[1
]}

Wolf, Christian ^{[1
]}

机构：

[1] Georgetown Univ, Dept Chem, Washington, DC 20057 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 14期

关键词：

D O I：

10.1021/ol071067v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-phosphinous acids catalyze the conjugate addition of arylsiloxanes to a wide range of alpha,beta-unsaturated substrates in water. A microwave-assisted procedure is described that uses 5 mol % of POPd1 to afford beta-substituted ketones, aldehydes, esters, nitriles, and nitroalkanes in 83% to 96% yield within 4 h. This method eliminates the need for stoichiometric additives and an excess of arylsiloxane, and does not require an inert atmosphere.

引用

页码：2737 / 2740

页数：4

共 48 条

[1] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES [J].

AHN, KH ;

KLASSEN, RB ;

LIPPARD, SJ .

ORGANOMETALLICS, 1990, 9 (12) :3178-3181

[2] Bonding modes in palladium(II) enolates:: Consequences for dynamic behavior and reactivity [J].

Albéniz, AC ;

Catalina, NM ;

Espinet, P ;

Redón, R .

ORGANOMETALLICS, 1999, 18 (26) :5571-5576

[3] [2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands [J].

Bigeault, J ;

Giordano, L ;

Buono, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) :4753-4757

[4] Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].

Cauble, DF ;

Gipson, JD ;

Krische, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111

[5] Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: Asymmetric synthesis of (R)-tolterodine [J].

Chen, G ;

Tokunaga, N ;

Hayashi, T .

ORGANIC LETTERS, 2005, 7 (11) :2285-2288

[6] Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes [J].

Denmark, SE ;

Amishiro, N .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6997-7003

[7] Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes:: A catalytic route to β2-amino acids, aldehydes, and alcohols [J].

Duursma, A ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3700-3701

[8] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

[9] Palladium-catalyzed enantioselective conjugate addition of arylboronic acids [J].

Gini, F ;

Hessen, B ;

Minnaard, AJ .

ORGANIC LETTERS, 2005, 7 (23) :5309-5312

[10] Enantioselective palladium-catalysed conjugate addition of arylsiloxanes [J].

Gini, Francesca ;

Hessen, Bart ;

Feringa, Ben L. ;

Minnaard, Adriaan J. .

CHEMICAL COMMUNICATIONS, 2007, (07) :710-712

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