Palladium-Catalyzed C-C Triple Bond Cleavage: Efficient Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones

被引：86

作者：

Liu, Qilun ^{[1
]}

Chen, Pinhong ^{[1
,2
]}

Liu, Guosheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Peoples R China

来源：

ACS CATALYSIS | 2013年 / 3卷 / 02期

基金：

美国国家科学基金会;

关键词：

Pd catalyst; azidoalkyne; aminocyclization; C-C triple bond cleavage; oxidation; LIPASE INHIBITOR; AMINOFLUORINATION; COMPLEXES; ALKYNE; TRANSFORMATION; CETILISTAT; ACCESS;

D O I：

10.1021/cs300733s

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Described herein is a new transformation of azidoalkynes by using a palladium catalyst, which involves a tandem process of aminopalladation of the alkyne and oxidative rearrangement. The reaction affords a variety of 4H-benzo[d][1,3]oxazin-4-ones. Mechanism studies support a Pd-catalyzed aminopalladation/oxidation/Baeyer-Villiger fragmentary sequence.

引用

页码：178 / 181

页数：4

共 37 条

[31] Gold-Catalyzed Transformation of 2-Alkynyl Arylazides: Efficient Access to the Valuable Pseudoindoxyl and Indolyl Frameworks [J].

Wetzel, Alexander ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) :7354-7358

[32] Palladium-Catalyzed Intramolecular Aminofluorination of Unactivated Alkenes [J].

Wu, Tao ;

Yin, Guoyin ;

Liu, Guosheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) :16354-+

[33] Ag(I)-Catalyzed Aminofluorination of Alkynes: Efficient Synthesis of 4-Fluoroisoquinolines and 4-Fluoropyrrolo[α]isoquinolines [J].

Xu, Tao ;

Liu, Guosheng .

ORGANIC LETTERS, 2012, 14 (21) :5416-5419

[34] Silver-Catalyzed Intramolecular Aminofluorination of Activated Allenes [J].

Xu, Tao ;

Mu, Xin ;

Peng, Haihui ;

Liu, Guosheng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (35) :8176-8179

[35] Cetilistat (ATL-962), a novel pancreatic lipase inhibitor, ameliorates body weight gain and improves lipid profiles in rats [J].

Yamada, Y. ;

Kato, T. ;

Ogino, H. ;

Ashina, S. ;

Kato, K. .

HORMONE AND METABOLIC RESEARCH, 2008, 40 (08) :539-543

[36] Halopalladation Cyclization of Alkynes with Azides: Selective Synthesis of 4-Haloisoquinolines and 3-Haloindoles [J].

Zhang, Hong-Ping ;

Yu, Shang-Ci ;

Liang, Yun ;

Peng, Peng ;

Tang, Bo-Xiao ;

Li, Jin-Heng .

SYNLETT, 2011, (07) :982-988

[37] Palladium-Catalyzed Oxidative Aminofluorination of Styrenes [J].

Zhu Haitao ;

Liu Guosheng .

ACTA CHIMICA SINICA, 2012, 70 (23) :2404-2407

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