Coupling Reaction of Cu-Based Carbene and Nitroso Radical: A Tandem Reaction To Construct Isoxazolines

被引：49

作者：

Chen, Rongxiang ^{[1
]}

Zhao, Yanwei ^{[1
]}

Fang, Shangwen ^{[1
]}

Long, Wenhao ^{[1
]}

Sun, Hongmei ^{[1
]}

Wan, Xiaobing ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 21期

关键词：

TERT-BUTYL NITRITE; CO(II)-BASED METALLORADICAL CATALYSIS; BETA-HYDROXY KETONES; GAMMA-AMINO KETONES; DIAZO-COMPOUNDS; H FUNCTIONALIZATION; FACILE SYNTHESIS; BOND FORMATION; UNACTIVATED ALKENES; DIRECT CONVERSION;

D O I：

10.1021/acs.orglett.7b02885

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this letter, an unprecedented cross-coupling reaction between copper carbene and nitroso radical has been developed: This radical-carbene coupling reaction (RCC reaction) offers a novel approach for the preparation of various isoxazolines, which features the construction of C-C, C-O, and C=N bonds in a one-pot process. The synthetic utility of our method is further enhanced by its mild reaction conditions, wide substrate scope, and simple procedures.

引用

页码：5896 / 5899

页数：4

共 89 条

[51] Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents [J].

Mendelsohn, Brian A. ;

Lee, Shelley ;

Kim, Simon ;

Teyssier, Florian ;

Aulakh, Virender S. ;

Ciufolini, Marco A. .

ORGANIC LETTERS, 2009, 11 (07) :1539-1542

[52] Tert-butyl nitrite: a metal-free radical initiator for aerobic cleavage of benzylic C=C bonds in compressed carbon dioxide [J].

Miao, Cheng-Xia ;

Yu, Bing ;

He, Liang-Nian .

GREEN CHEMISTRY, 2011, 13 (03) :541-544

[53] Generation of Nitrile Oxides from Oximes Using t-BuOI and Their Cycloaddition [J].

Minakata, Satoshi ;

Okumura, Sota ;

Nagamachi, Toshiki ;

Takeda, Youhei .

ORGANIC LETTERS, 2011, 13 (11) :2966-2969

[54] A concise approach to structurally diverse β-amino acids [J].

Minter, AR ;

Fuller, AA ;

Mapp, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (23) :6846-6847

[55] Mechanism of C-H bond activation/C-C bond formation reaction between diazo compound and alkane catalyzed by dirhodium tetracarboxylate [J].

Nakamura, E ;

Yoshikai, N ;

Yamanaka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) :7181-7192

[56] Role of Sterically Demanding Chiral Dirhodium Catalysts in Site-Selective C-H Functionalization of Activated Primary C-H Bonds [J].

Qin, Changming ;

Davies, Huw M. L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (27) :9792-9796

[57] Specific, uncompetitive inhibition of β-galactosidases by a 5,6-isopropylidenedioxyfuro[2,3-d]isoxazole-3-methanol derivative [J].

Schaller, C ;

Demange, R ;

Picasso, S ;

Vogel, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) :277-278

[58] Palladium(II)-Catalyzed Direct Conversion of Methyl Arenes into Aromatic Nitriles [J].

Shu, Zhibin ;

Ye, Yuxuan ;

Deng, Yifan ;

Zhang, Yan ;

Wang, Jianbo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) :10573-10576

[59] Tin-free radical chemistry using the persistent radical effect: alkoxyamine isomerization, addition reactions and polymerizations [J].

Studer, A .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (05) :267-273

[60]

Studer A, 2001, CHEM-EUR J, V7, P1159, DOI 10.1002/1521-3765(20010316)7:6<1159::AID-CHEM1159>3.3.CO

← 1 2 3 4 5 6 7 8 9 →