Palladium-Catalyzed α-Arylation of Benzylic Phosphonates

被引：45

作者：

Montel, Sonia ^{[1
]}

Raffier, Ludovic ^{[1
]}

He, Yuying ^{[1
]}

Walsh, Patrick J. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Penn Merck Lab High Throughput Expt, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 05期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

CARBANIONS; SULFOXIDES; COMPLEXES; AMIDES;

D O I：

10.1021/ol5002413

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic route to access diarylmethyl phosphonates is presented. The transformation enables the introduction of aromatic groups on benzylic phosphonates via a deprotonative cross-coupling process (DCCP). The Pd(OAc)(2)/CataCXium A-based catalyst afforded a reaction between benzyl diisopropyl phosphonate derivatives and aryl bromides in good to excellent isolated yields (64-92%).

引用

页码：1446 / 1449

页数：4

共 35 条

[1] Photochemical vinylcyclopropane rearrangements of 1-substituted-3-(2,2-diphenylvinyl)-2,2-dimethylcyclopropanes to cyclopentenes and different heterocycles [J].

Armesto, D ;

Ortiz, MJ ;

Agarrabeitia, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1056-1060

[2]

Arrachart G., 2013, Patent, Patent No. [WO2013167516 A1 20131114, 201316716]

[3] Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes [J].

Bellomo, Ana ;

Zhang, Jiadi ;

Trongsiriwat, Nisalak ;

Walsh, Patrick J. .

CHEMICAL SCIENCE, 2013, 4 (02) :849-857

[4]

BIELLMANN JF, 1982, ORG REACTIONS, V27, P1

[5]

Bisceglia JA, 2012, CURR ORG CHEM, V16, P2206

[6] Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group [J].

Demmer, Charles S. ;

Krogsgaard-Larsen, Niels ;

Bunch, Lennart .

CHEMICAL REVIEWS, 2011, 111 (12) :7981-8006

[7]

Georlette P., 2013, Patent, Patent No. [WO2013176868 A1 20131128, 2013176868]

[8] Zn(tmp)2:: A versatile base for the selective functionalization of C-H bonds [J].

Hlavinka, Mark L. ;

Hagadorn, John R. .

ORGANOMETALLICS, 2007, 26 (17) :4105-4108

[9]

Jackson ER, 2012, CURR TOP MED CHEM, V12, P706

[10] Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single PalladiumCatalyzed Triple Relay Process [J].

Jia, Tiezheng ;

Bellomo, Ana ;

Montel, Sonia ;

Zhang, Mengnan ;

Baina, Kawtar E. L. ;

Zheng, Bing ;

Walsh, Patrick J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :260-264

← 1 2 3 4 →