Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions

被引：18

作者：

Cao, Dawei ^{[1
,2
,3
,4
,5
]}

Xia, Shumei ^{[4
,5
]}

Pan, Pan ^{[3
]}

Zeng, Huiying ^{[3
]}

Li, Chao-Jun ^{[4
,5
]}

Peng, Yong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Sch Phys Sci & Technol, Key Lab Magnetism & Magnet Mat, Minist Educ, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Electron Microscopy Ctr, Lanzhou 730000, Peoples R China

[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[4] McGill Univ, Dept Chem, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada

[5] McGill Univ, FRQNT Ctr Green Chem & Catalysis, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada

来源：

GREEN CHEMISTRY | 2021年 / 23卷 / 19期

基金：

加拿大自然科学与工程研究理事会; 中国国家自然科学基金;

关键词：

FUNCTIONALIZATION; HYDROGENATION; CONVERSION; CATALYSIS; RADICALS; REAGENTS; KETONES; BONDS;

D O I：

10.1039/d1gc02449c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.

引用

页码：7539 / 7543

页数：5

共 38 条

[1] Asymmetric homogeneous hydrogenations at scale [J].

Ager, David J. ;

de Vries, Andre H. M. ;

de Vries, Johannes G. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3340-3380

[2] Catalytic Conversion of Nonfood Woody Biomass Solids to Organic Liquids [J].

Barta, Katalin ;

Ford, Peter C. .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1503-1512

[3] Industrial methods for the production of optically active intermediates [J].

Breuer, M ;

Ditrich, K ;

Habicher, T ;

Hauer, B ;

Kesseler, M ;

Stürmer, R ;

Zelinski, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :788-824

[4] Boron reagents in process chemistry: Excellent tools for selective reductions [J].

Burkhardt, Elizabeth R. ;

Matos, Karl .

CHEMICAL REVIEWS, 2006, 106 (07) :2617-2650

[5] Light-Driven Metal-Free Direct Deoxygenation of Alcohols under Mild Conditions [J].

Cao, Dawei ;

Chen, Zhangpei ;

Lv, Leiyang ;

Zeng, Huiying ;

Peng, Yong ;

Li, Chao-Jun .

ISCIENCE, 2020, 23 (08)

[6] Hydrogen bonding promoted simple and clean photo-induced reduction of C-X bond with isopropanol [J].

Cao, Dawei ;

Yan, Chaoxian ;

Zhou, Panpan ;

Zeng, Huiying ;

Li, Chao-Jun .

CHEMICAL COMMUNICATIONS, 2019, 55 (06) :767-770

[7] Photocatalytic three-component asymmetric sulfonylation via direct C(sp3)-H functionalization [J].

Cao, Shi ;

Hong, Wei ;

Ye, Ziqi ;

Gong, Lei .

NATURE COMMUNICATIONS, 2021, 12 (01)

[8] Visible light photoredox-controlled reactions of N-radicals and radical ions [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056

[9] Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels [J].

Climent, Maria J. ;

Corma, Avelino ;

Iborra, Sara .

GREEN CHEMISTRY, 2014, 16 (02) :516-547

[10] PHOTOREDUCTION BY AMINES [J].

COHEN, SG ;

PAROLA, A ;

PARSONS, GH .

CHEMICAL REVIEWS, 1973, 73 (02) :141-161

← 1 2 3 4 →