Heteroarylation of Ethers, Amides, and Alcohols with Light and O2

被引：25

作者：

Bhakat, Manotosh ^{[1
]}

Biswas, Promita ^{[1
]}

Dey, Jayanta ^{[1
]}

Guin, Joyram ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Sch Chem Sci, Kolkata 700032, India

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 17期

关键词：

DIRECT ALPHA-ARYLATION; C-H ALKYLATION; C(SP(3))-H BONDS; MINISCI REACTION; SINGLET OXYGEN; METAL-FREE; OXIDATIONS; CATALYSIS; AZIDE;

D O I：

10.1021/acs.orglett.1c02440

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol for the C-alpha-H heteroarylation of ethers, amides, and alcohols using air and light under mild conditions is described. The reaction is applicable to a wide spectrum of functional groups. The generation of C-radicals via photoinduced aerobic oxidation of ethers, amides, and alcohols is the key feature of the process. Control experiments suggest a radical pathway for the reaction.

引用

页码：6886 / 6890

页数：5

共 40 条

[1] Sodium azide as a specific quencher of singlet oxygen during chemiluminescent detection by luminol and Cypridina luciferin analogues [J].

Bancirova, Martina .

LUMINESCENCE, 2011, 26 (06) :685-688

[2] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, Kenneth W. .

NATURAL PRODUCT REPORTS, 2006, 23 (03) :444-463

[3] Minisci-Photoredox-Mediated α-Heteroarylation of N-Protected Secondary Amines: Remarkable Selectivity of Azetidines [J].

Bosset, Cyril ;

Beucher, Helene ;

Bretel, Guillaume ;

Pasquier, Elisabeth ;

Queguiner, Laurence ;

Henry, Cyril ;

Vos, Ann ;

Edwards, James P. ;

Meerpoel, Lieven ;

Berthelot, Didier .

ORGANIC LETTERS, 2018, 20 (19) :6003-6006

[4] Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].

Campbell, Alison N. ;

Stahl, Shannon S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863

[5] Metal-free, hydroacylation of C=C and N=N bonds via aerobic C-H activation of aldehydes, and reaction of the products thereof [J].

Chudasama, Vijay ;

Akhbar, Ahmed R. ;

Bahou, Karim A. ;

Fitzmaurice, Richard J. ;

Caddick, Stephen .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (42) :7301-7317

[6] Iron-catalyzed direct α-arylation of ethers with azoles [J].

Correa, Arkaitz ;

Fiser, Bela ;

Gomez-Bengoa, Enrique .

CHEMICAL COMMUNICATIONS, 2015, 51 (69) :13365-13368

[7] Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation [J].

Das, Prasenjit ;

Saha, Debajyoti ;

Saha, Dibyajyoti ;

Guin, Joyram .

ACS CATALYSIS, 2016, 6 (09) :6050-6054

[8] Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines [J].

Dong, Jianyang ;

Xia, Qing ;

Lv, Xueli ;

Yang, Changcun ;

Song, Hongjian ;

Liu, Yuxiu ;

Wang, Qingmin .

ORGANIC LETTERS, 2018, 20 (18) :5661-5665

[9] INVOLVEMENT OF THE AZIDE RADICAL IN THE QUENCHING OF SINGLET OXYGEN BY AZIDE ANION IN WATER [J].

HARBOUR, JR ;

ISSLER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (03) :903-905

[10] The Use of Molecular Oxygen for Liquid Phase Aerobic Oxidations in Continuous Flow [J].

Hone, Christopher A. ;

Kappe, C. Oliver .

TOPICS IN CURRENT CHEMISTRY, 2019, 377 (01)

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