Chelation-assisted palladium-catalyzed acyloxylation of benzyl sp3 C-H bonds using PhI(OAc)2 as oxidant

被引：43

作者：

Zhang, Shouhui ^{[1
]}

Luo, Fang ^{[1
]}

Wang, Wenhui ^{[1
]}

Jia, Xiaofei ^{[1
]}

Hu, Maolin ^{[1
]}

Cheng, Jiang ^{[1
,2
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325027, Peoples R China

[2] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 25期

基金：

中国国家自然科学基金;

关键词：

FORMING REDUCTIVE ELIMINATION; OXIDATIVE FUNCTIONALIZATION; COUPLING REACTIONS; ACETOXYLATION; AMINOACETOXYLATION; REGIOSELECTIVITY; REAGENTS; PD(II);

D O I：

10.1016/j.tetlet.2010.04.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chelation-assisted palladium-catalyzed acyloxylation of the sp(3) C-H bond of benzyl by carboxylic acid is described, which employs PhI(OAc)(2) as a stoichiometric oxidant. The procedure tolerates a series of functional groups, such as methoxyl, chloro, bromo, iodo, vinyl, formyl, phenolic hydroxyl, nitro, and cyano groups, providing the acyloxylation products in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3317 / 3319

页数：3

共 49 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[2] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].

Alexanian, EJ ;

Lee, C ;

Sorensen, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691

[3] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex [J].

Ball, Nicholas D. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3796-+

[4]

Chatani N, 2007, TOP ORGANOMETAL CHEM, V24, P1, DOI 10.1007/978-3-540-75809-9

[5] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].

Chen, X ;

Li, JJ ;

Hao, XS ;

Goodhue, CE ;

Yu, JQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79

[6] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[8] Regioselective functionalization of unreactive carbon-hydrogen bonds [J].

Daugulis, Olafs ;

Zaitsev, Vladimir G. ;

Shabashov, Dmitry ;

Pham, Quynh-Nhu ;

Lazareva, Anna .

SYNLETT, 2006, (20) :3382-3388

[9] Reactions of hypervalent iodine reagents with palladium: Mechanisms and applications in organic synthesis [J].

Deprez, Nicholas R. ;

Sanford, Melanie S. .

INORGANIC CHEMISTRY, 2007, 46 (06) :1924-1935

[10] Insights into directing group ability in palladium-catalyzed C-H bond functionalization [J].

Desai, Lopa V. ;

Stowers, Kara J. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) :13285-13293

← 1 2 3 4 5 →