Radical Hydroalkylation and Hydroacylation of Alkenes by the Use of Benzothiazoline under Thermal Conditions

被引：20

作者：

Uchikura, Tatsuhiro ^{[1
]}

Toda, Mitsuhiro ^{[1
]}

Mouri, Toshiki ^{[1
]}

Fujii, Tatsuya ^{[1
]}

Moriyama, Kaworuko ^{[1
]}

Ibanez, Ignacio ^{[1
]}

Akiyama, Takahiko ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 19期

关键词：

MERGING PHOTOREDOX; NICKEL CATALYSIS; ALKYL TRANSFER; ACYLATION; ACID; REDUCTION; ESTERS;

D O I：

10.1021/acs.joc.0c01872

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroalkylation and hydroacylation of electrondeficient alkenes proceeded smoothly by using benzothiazoline derivatives as radical-transfer reagents under thermal conditions without light irradiation or any additive. Both benzyl and benzoyl moieties were transferred efficiently.

引用

页码：12715 / 12723

页数：9

共 46 条

[1] Radical transfer hydrosilylation/cyclization using silylated cyclohexadienes [J].

Amrein, S ;

Timmermann, A ;

Studer, A .

ORGANIC LETTERS, 2001, 3 (15) :2357-2360

[2]

[Anonymous], 2000, WLR

[3]

Ballesteros P., 1986, Org. Synth, V64, P63

[4] Acyl Radical Chemistry via Visible-Light Photoredox Catalysis [J].

Banerjee, Arghya ;

Lei, Zhen ;

Ngai, Ming-Yu .

SYNTHESIS-STUTTGART, 2019, 51 (02) :303-333

[5] SOLVENT DEGASSING AND OTHER FACTORS AFFECTING LIQUID-CHROMATOGRAPHIC DETECTOR STABILITY [J].

BROWN, JN ;

HEWINS, M ;

VANDERLINDEN, JHM ;

LYNCH, RJ .

JOURNAL OF CHROMATOGRAPHY, 1981, 204 (JAN) :115-122

[6] Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids [J].

Capaldo, Luca ;

Buzzetti, Luca ;

Merli, Daniele ;

Fagnoni, Maurizio ;

Ravelli, Davide .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :7102-7109

[7] Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis [J].

Chen, Wenxin ;

Liu, Zheng ;

Tian, Jiaqi ;

Li, Jin ;

Ma, Jing ;

Cheng, Xu ;

Li, Guigen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (38) :12312-12315

[8] Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids [J].

Chu, Lingling ;

Lipshultz, Jeffrey M. ;

MacMillan, David W. C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) :7929-7933

[9]

Chudasama V, 2010, NAT CHEM, V2, P592, DOI [10.1038/NCHEM.685, 10.1038/nchem.685]

[10] Visible-Light-Activated Catalytic Enantioselective β-Alkylation of α, β-Unsaturated 2-Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs [J].

de Assis, Francisco F. ;

Huang, Xiaoqiang ;

Akiyama, Midori ;

Pilli, Ronaldo A. ;

Meggers, Eric .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (18) :10922-10932

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