Palladium-catalyzed R2(O)P directed C(sp2)-H acetoxylation

被引：69

作者：

Zhang, Heng ^{[1
]}

Hu, Rong-Bin ^{[1
]}

Zhang, Xiao-Yu ^{[1
]}

Li, Shi-Xia ^{[1
]}

Yang, Shang-Dong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 36期

关键词：

PALLADIUM(II)-CATALYZED ORTHO-ARYLATION; ARYL HYDROGEN PHOSPHATES; C-H FUNCTIONALIZATION; ORTHO-ALKENYLATION; COUPLING REACTIONS; BOND FORMATION; O BOND; OXIDATION; DIBENZOFURANS; ACTIVATION;

D O I：

10.1039/c4cc01238k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel and efficient Pd-catalyzed C-H acetoxylation is described. The approach uses R-2(O)P as a directing group to synthesize various substituted 2'-phosphorylbiphenyl-2-OAc compounds. Notably, the reaction exhibits smooth operation under mild conditions and shows good functional group tolerance. Products are obtained with high selectivity and yields.

引用

页码：4686 / 4689

页数：4

共 67 条

[21] C-H functionalization logic in total synthesis [J].

Gutekunst, Will R. ;

Baran, Phil S. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1976-1991

[22]

Hartwig J.F., 2002, Handbook of Organopalladium Chemistry for Organic Synthesis, V1, P1097, DOI DOI 10.1002/0471212466.CH43

[23] Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions [J].

Hayashi, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :354-362

[24] Palladium-catalyzed P(O)R2 directed C-H arylation to synthesize electron-rich polyaromatic monophosphorus ligands [J].

Hu, Rong-Bin ;

Zhang, Heng ;

Zhang, Xiao-Yu ;

Yang, Shang-Dong .

CHEMICAL COMMUNICATIONS, 2014, 50 (17) :2193-2195

[25] An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters [J].

Huang, Zhiyan ;

Liu, Zheng ;

Zhou, Jianrong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (40) :15882-15885

[26] Highly regioselective catalytic oxidative coupling reactions: Synthetic and mechanistic investigations [J].

Hull, Kami L. ;

Lanni, Erica L. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14047-14049

[27] Ruthenium-Catalyzed ortho-Alkenylation of Phenylphosphine Oxides through Regio- and Stereoselective Alkyne Insertion into C-H Bonds [J].

Itoh, Masaki ;

Hashimoto, Yuto ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) :8098-8104

[28] Palladium(II)-catalyzed ortho-arylation via phosphate-group-directed C-H activation [J].

Jeon, Woo Hyung ;

Lee, Tae Seob ;

Kim, Eun Jin ;

Moon, Bongjin ;

Kang, Jahyo .

TETRAHEDRON, 2013, 69 (25) :5152-5159

[29] Regioselectivity in palladium-catalyzed C-H activation/oxygenation reactions [J].

Kalyani, D ;

Sanford, MS .

ORGANIC LETTERS, 2005, 7 (19) :4149-4152

[30] Beyond Directing Groups: Transition-Metal-Catalyzed C-H Activation of Simple Arenes [J].

Kuhl, Nadine ;

Hopkinson, Matthew N. ;

Wencel-Delord, Joanna ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) :10236-10254

← 1 2 3 4 5 6 7 →