Radical-Mediated Distal Ipso-Migration of O/S-Containing Heteroaryls and DFT Studies for Migratory Aptitude

被引：40

作者：

Zhang, Huihui ^{[1
]}

Kou, Luyao ^{[1
]}

Chen, Dong ^{[1
]}

Ji, Meishan ^{[1
]}

Bao, Xiaoguang ^{[1
]}

Wu, Xinxin ^{[1
]}

Zhu, Chen ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 15期

基金：

中国国家自然科学基金;

关键词：

UNACTIVATED ALKENES; DIFUNCTIONALIZATION; CYCLIZATION; FUNCTIONALIZATION; ALKYNYLATION; FLUORINE; STRATEGY; OLEFIN;

D O I：

10.1021/acs.orglett.0c02030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe an efficient distal ipso-migration of O- and S-containing heteroaryls and the radical heteroarylation of unactivated alkenes. The migration is triggered by various fluoroalkyl radicals, leading to valuable multifunctionalized ketones. The comparisons of migratory aptitude for O-/S-containing heteroaryls are comprehensively investigated. The origin of the chemoselective migration could be partially attributed to the discrepancy in the energy level of the LUMO of each heteroaryl group.

引用

页码：5947 / 5952

页数：6

共 54 条

[1]

[Anonymous], 2004, ChemBioChem, V5, P557

[2] Molecular Oxygen Mediated Radical Dicarbofunctionalization of Olefin with Aldehyde [J].

Biswas, Promita ;

Guin, Joyram .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) :5629-5638

[3] The fluorous effect in biomolecular applications [J].

Cametti, Massimo ;

Crousse, Benoit ;

Metrangolo, Pierangelo ;

Milani, Roberto ;

Resnati, Giuseppe .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :31-42

[4] Olefin difunctionalizations via visible light photocatalysis [J].

Cao, Min-Yi ;

Ren, Xiang ;

Lu, Zhan .

TETRAHEDRON LETTERS, 2015, 56 (24) :3732-3742

[5] Difunctionalization of Unactivated Alkenes through SCF3 Radical-triggered Distal Functional Group Migration [J].

Chen Dong ;

Ji Meishan ;

Yao Yingming ;

Zhu Chen .

ACTA CHIMICA SINICA, 2018, 76 (12) :951-955

[6] Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration [J].

Chen, Dong ;

Wu, Zhen ;

Yao, Yingming ;

Zhu, Chen .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (15) :2370-2374

[7] Radical aryl migration reactions and synthetic applications [J].

Chen, Zhi-Min ;

Zhang, Xiao-Ming ;

Tu, Yong-Qiang .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (15) :5220-5245

[8]

Clark A. J, 2016, EUR J ORG CHEM, V2016, P2231

[9] Copper Catalyzed Atom Transfer Radical Addition (ATRA) and Cyclization (ATRC) Reactions in the Presence of Reducing Agents [J].

Eckenhoff, William T. ;

Pintauer, Tomislav .

CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2010, 52 (01) :1-59

[10] Cyclization Cascades via N-Amidyl Radicals toward Highly Functionalized Heterocyclic Scaffolds [J].

Fuentes, Noelia ;

Kong, Wangqing ;

Fernandez-Sanchez, Luis ;

Merino, Estibaliz ;

Nevado, Cristina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (02) :964-973

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