Palladium-Catalyzed Synthesis of Diarylmethanes: Exploitation of Carbanionic Leaving Groups

被引：40

作者：

Schmink, Jason R. ^{[1
]}

Leadbeater, Nicholas E. ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 12期

关键词：

CROSS-COUPLING REACTIONS; ALPHA-ARYLATION; ARYLBORONIC ACIDS; KETONES; ARYL; HALIDES;

D O I：

10.1021/ol900874z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to the synthesis of diarylmethanes via a Pd-catalyzed alpha-arylation of benzyl ketones is reported. By harnessing the inherent reactivity of enolates, it is possible to circumvent the need for a transmetalating reagent such as boron for the coupling. Additionally, the two phenyl rings of the intermediate are exploited to stabilize the high-energy carbanionic leaving group in a straightforward synthesis.

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页码：2575 / 2578

页数：4

相关论文

共 18 条

[1] Microwave-promoted Heck coupling using ultralow metal catalyst concentrations [J].

Arvela, RK ;

Leadbeater, NE .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05) :1786-1790

[2] A reassessment of the transition-metal free Suzuki-type coupling methodology [J].

Arvela, RK ;

Leadbeater, NE ;

Sangi, MS ;

Williams, VA ;

Granados, P ;

Singer, RD .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168

[3] Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners [J].

Burns, Michael J. ;

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Sehnal, Petr ;

Taylor, Richard J. K. .

ORGANIC LETTERS, 2007, 9 (26) :5397-5400

[4] Palladium-Catalyzed Cross-Coupling Reactions of Benzyl Indium Reagents with Aryl Iodides [J].

Chupak, Louis S. ;

Wolkowski, Joanna P. ;

Chantigny, Yves A. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1388-1390

[5] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[6] α-arylation of ketones using highly active, air-stable (DtBPF)PdX2 (X = cl, br) catalysts [J].

Grasa, Gabriela A. ;

Colacot, Thomas J. .

ORGANIC LETTERS, 2007, 9 (26) :5489-5492

[7] α-arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)3]PdBr}2 [J].

Hama, Takuo ;

Hartwig, John F. .

ORGANIC LETTERS, 2008, 10 (08) :1545-1548

[8] Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383

[9]

Lagrave R, 1927, ANN CHIM FRANCE, V8, P363

[10] Fast, easy, clean chemistry by using water as a solvent and microwave heating: the Suzuki coupling as an illustration [J].

Leadbeater, NE .

CHEMICAL COMMUNICATIONS, 2005, (23) :2881-2902