Nickel-Catalyzed Hydroamination and Hydroalkoxylation of Enelactams with Unactivated Amines and Alcohols

被引：4

作者：

Song, Tao ^{[1
]}

Wang, Kuiyang ^{[1
]}

Yuan, Qianjia ^{[1
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Frontiers Sci Ctr, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 32期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

OLEFINS; FUNCTIONALIZATION; ALKYLATION; ARYLATION; ALKENES; REMOTE;

D O I：

10.1021/acs.orglett.3c02341

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel-catalyzedhydroamination and hydroalkoxylation of enelactamswith unactivated amines and alcohols are reported. This method showedgood functional group tolerance and delivered the corresponding hydrofunctionalizedproducts in good to excellent yields (& LE;98%). Furthermore, anintramolecular hydroalkoxylation of an enelactam was also realized,giving a cyclization product in a good yield. Mechanistic studiesindicated that tBuI acts as a hydride donor and radicalprecursor, which is crucial for the success of the reaction.

引用

收藏

页码：6093 / 6098

页数：6

相关论文

共 64 条

[1] Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design [J].

Adamson, Nathan J. ;

Jeddi, Haleh ;

Malcolmson, Steven J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (21) :8574-8583

[2] Alkyne and Alkene Insertion into Metal-Heteroatom and Metal-Hydrogen Bonds: The Key Stages of Hydrofunctionalization Process [J].

Ananikov, Valentine P. ;

Beletskaya, Irina P. .

HYDROFUNCTIONALIZATION, 2013, 43 :1-19

[3] SYNERAZOL, A NEW ANTIFUNGAL ANTIBIOTIC [J].

ANDO, O ;

SATAKE, H ;

NAKAJIMA, M ;

SATO, A ;

NAKAMURA, T ;

KINOSHITA, T ;

FURUYA, K ;

HANEISHI, T .

JOURNAL OF ANTIBIOTICS, 1991, 44 (04) :382-389

[4] Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters [J].

Bera, Srikrishna ;

Hu, Xile .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (39) :13854-13859

[5] Enantioselective Synthesis of α,β-Unsaturated Aryl Lactams by Heck-Matsuda and Heck-Mizoroki Arylations of Enelactams [J].

Braga, Ingredy Bastos ;

Angnes, Ricardo Almir ;

de Lucca Junior, Emilio Carlos ;

Carmo Braga, Ataualpa Albert ;

Duarte Correia, Carlos Roque .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (39)

[6] Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes [J].

Chen, Yue-Gang ;

Shuai, Bin ;

Xu, Xue-Tao ;

Li, Yi-Qian ;

Yang, Qi-Liang ;

Qiu, Hui ;

Zhang, Kun ;

Fang, Ping ;

Mei, Tian-Sheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) :3395-3399

[7] Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides [J].

Cuesta-Galisteo, Sergio ;

Schorgenhumer, Johannes ;

Wei, Xiaofeng ;

Merino, Estibaliz ;

Nevado, Cristina .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (03) :1605-1609

[8] Design, synthesis and antifungal activity of pterolactam-inspired amide Mannich bases [J].

Dascalu, Anca-Elena ;

Ghinet, Alina ;

Lipka, Emmanuelle ;

Furman, Christophe ;

Rigo, Benoit ;

Fayeulle, Antoine ;

Billamboz, Muriel .

FITOTERAPIA, 2020, 143

[9] Nickel-Catalyzed, Enantioselective Hydrofluoromethylation of Olefins: Access to Chiral ?-Fluoromethylated Amides and Esters [J].

Du, Yiming ;

Chen, Shuxin ;

Cao, Hexiang ;

Zhang, Yichen ;

Lei, Hongtao ;

Xia, Guoqin ;

Huang, Huicai ;

Li, Zhaodong .

ORGANIC LETTERS, 2023, 25 (13) :2218-2222

[10] NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines [J].

Gao, Yang ;

Yang, Simin ;

Huo, Yanping ;

Chen, Qian ;

Li, Xianwei ;

Hu, Xiao-Qiang .

ACS CATALYSIS, 2021, 11 (13) :7772-7779

← 1 2 3 4 5 6 7 →