Autocatalytic aerobic ipso-hydroxylation of arylboronic acid with Hantzsch ester and Hantzsch pyridine

被引：10

作者：

Fan, Chi-Hang ^{[1
,2
]}

Xu, Tianyue ^{[1
,2
]}

Ke, Zhihai ^{[3
]}

Yeung, Ying-Yeung ^{[1
,2
]}

机构：

[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[2] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Shatin, Hong Kong, Peoples R China

[3] Chinese Univ Hong Kong, Sch Sci & Engn, Shenzhen 518172, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 15期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; OXIDATIVE HYDROXYLATION; ELECTRON-TRANSFER; METAL-FREE; CATALYZED HYDROXYLATION; PHOTOREDOX CATALYSIS; PHENOLS; ARYL; NANOPARTICLES; CONVERSION;

D O I：

10.1039/d2qo00618a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hantzsch esters are very useful hydrogen and electron donors that have been applied in many reactions. After the reactions, aromatic Hantzsch pyridines are generated as the by-products and their roles are commonly ignored. Herein, we report the use of Hantzsch pyridine as a promoter to activate Hantzsch ester in the generation of the hydrogen peroxy radical, which is useful for the ipso-hydroxylation of arylboronic acids to give phenols. The reaction does not require an external catalyst or light. The conditions are mild and highly compatible with different functional groups.

引用

页码：4091 / 4096

页数：6

共 45 条

[1] Oxidative hydroxylation of arylboronic acids to phenols catalyzed by copper nanoparticles ellagic acid composite [J].

Affrose, Abdullah ;

Azath, Ismail Abulkalam ;

Dhakshinamoorthy, Amarajothi ;

Pitchumani, Kasi .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 395 :500-505

[2] Electron transfer and singlet oxygen mechanisms in the photooxygenation of dibutyl sulfide and thioanisole in MeCN sensitized by N-methylquinolinium tetrafluoborate and 9,10-dicyanoanthracene.: The probable involvement of a thiadioxirane intermediate in electron transfer photooxygenations [J].

Baciocchi, E ;

Del Giacco, T ;

Elisei, F ;

Gerini, MF ;

Guerra, M ;

Lapi, A ;

Liberali, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16444-16454

[3] Catalysis by mont K-10 supported silver nanoparticles: a rapid and green protocol for the efficient ipso-hydroxylation of arylboronic acids [J].

Begum, Tahshina ;

Gogoi, Ankur ;

Gogoi, Pradip K. ;

Bora, Utpal .

TETRAHEDRON LETTERS, 2015, 56 (01) :95-97

[4]

Bockman TM, 1997, J PHYS ORG CHEM, V10, P542

[5] Photosensitized oxidation of sulfides: Discriminating between the singlet-oxygen mechanism and electron transfer involving superoxide anion or molecular oxygen [J].

Bonesi, Sergio M. ;

Manet, Ilse ;

Freccero, Mauro ;

Fagnoni, Maurizio ;

Albini, Angelo .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (18) :4844-4857

[6] Radical-Based C-C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines [J].

Buzzetti, Luca ;

Prieto, Alexis ;

Roy, Sudipta Raha ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) :15039-15043

[7] Organic hypervalent iodine(III) catalyzed ipso-hydroxylation of aryl- and alkylboronic acids/esters [J].

Chatterjee, Nachiketa ;

Goswami, Avijit .

TETRAHEDRON LETTERS, 2015, 56 (12) :1524-1527

[8] Oxygenation of Organoboronic Acids by a Nonheme Iron(II) Complex: Mimicking Boronic Acid Monooxygenase Activity [J].

Chatterjee, Sayanti ;

Paine, Tapan Kanti .

INORGANIC CHEMISTRY, 2015, 54 (20) :9727-9732

[9] A Mild and Highly Efficient Conversion of Arylboronic Acids into Phenols by Oxidation with MCPBA [J].

Chen, Dong-Song ;

Huang, Jing-Mei .

SYNLETT, 2013, 24 (04) :499-501

[10] Benzoquinone-Promoted Aerobic Oxidative Hydroxylation of Arylboronic Acids in Water [J].

Cheng, Guolin ;

Zeng, Xiaobao ;

Cui, Xiuling .

SYNTHESIS-STUTTGART, 2014, 46 (03) :295-300

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