Visible-light photoredox-promoted desilylative allylation of α-silylamines: An efficient route to synthesis of homoallylic amines

被引：41

作者：

Fan, Lulu ^{[1
]}

Cheng, Fukun ^{[1
]}

Zhang, Tingting ^{[1
]}

Liu, Guoxing ^{[2
]}

Yuan, Jinwei ^{[1
]}

Mao, Pu ^{[1
]}

机构：

[1] Henan Univ Technol, Coll Chem & Chem Engn, Zhengzhou 450001, Peoples R China

[2] Henan Agr Univ, Coll Sci, Zhengzhou 450002, Henan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2021年 / 81卷

基金：

中国国家自然科学基金;

关键词：

Visible-light photoredox catalysis; Homoallylic amines; Desilylative allylation; alpha-Amino alkyl radical; IMINO-ENE REACTIONS; AMINOALKYL RADICALS; DECARBOXYLATIVE ALLYLATION; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; MEDIATED ADDITION; CATALYSIS; ACIDS; STRATEGY; COMPLEX;

D O I：

10.1016/j.tetlet.2021.153357

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of homoallylic amines by visible-light photoredox-promoted desilylative allylation of alpha-silylamines with allylic sulfones is described. A variety of alpha-silylamines derived from anilines, cyclic and acyclic alkyl amines reacted with a serious of mono or disubstituted allylic sulfones well to provide homollylic amines in good to high yields under very mild reaction conditions. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：4

共 71 条

[51] Recent advancements in the homoallylamine chemistry [J].

Puentes, CO ;

Kouznetsov, V .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (04) :595-614

[52] Recent developments in the chiral synthesis of homoallylic amines via organoboranes [J].

Ramachandrant, P. Veeraraghavan ;

Burghardt, Thomas E. .

PURE AND APPLIED CHEMISTRY, 2006, 78 (07) :1397-1406

[53] Allylation of Imines and Their Derivatives with Organoboron Reagents: Stereocontrolled Synthesis of Homoallylic Amines [J].

Ramadhar, Timothy R. ;

Batey, Robert A. .

SYNTHESIS-STUTTGART, 2011, (09) :1321-1346

[54] Aminomethylation of Aryl Halides Using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis [J].

Remeur, Camille ;

Kelly, Christopher B. ;

Patel, Niki R. ;

Molander, Gary A. .

ACS CATALYSIS, 2017, 7 (09) :6065-6069

[55] A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions [J].

Shen, Xiang ;

Li, Yanjun ;

Wen, Zhaorui ;

Cao, Shi ;

Hou, Xinyi ;

Gong, Lei .

CHEMICAL SCIENCE, 2018, 9 (20) :4562-4568

[56] Direct Enantioselective C(sp3)-H Acylation for the Synthesis of α-Amino Ketones [J].

Shu, Xiaomin ;

Huan, Leitao ;

Huang, Qian ;

Huo, Haohua .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (45) :19058-19064

[57] Total Synthesis of (-)-Leuconicine A and B [J].

Sirasani, Gopal ;

Andrade, Rodrigo B. .

ORGANIC LETTERS, 2011, 13 (17) :4736-4737

[58] Palladium/Light Induced Radical Alkenylation and Allylation of Alkyl Iodides Using Alkenyl and Allylic Sulfones [J].

Sumino, Shuhei ;

Uno, Misae ;

Huang, Hsin-Ju ;

Wu, Yen-Ku ;

Ryu, Ilhyong .

ORGANIC LETTERS, 2018, 20 (04) :1078-1081

[59] Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids [J].

Wang, Lu ;

Lu, Chengrong ;

Yue, Yanni ;

Feng, Chao .

ORGANIC LETTERS, 2019, 21 (10) :3514-3517

[60] The recent achievements of redox-neutral radical C-C cross-coupling enabled by visible-light [J].

Xie, Jin ;

Jin, Hongming ;

Hashmi, A. Stephen K. .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (17) :5193-5203

← 1 2 3 4 5 6 7 8 →