Green Approach for Visible-Light-Induced Direct Functionalization of 2-Methylquinolines

被引：6

作者：

Dantas, Juliana A. ^{[1
]}

Echemendia, Radell ^{[1
]}

Santos, Marilia S. ^{[1
]}

Paixao, Marcio W. ^{[1
]}

Ferreira, Marco Antonio B. ^{[1
]}

Correa, Arlene G. ^{[1
]}

机构：

[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, Chem Dept, BR-13565905 Sao Carlos, SP, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 18期

基金：

巴西圣保罗研究基金会;

关键词：

METHYL AZAARENES; PHOTOCHEMISTRY; HETEROARENES; ALKYLATION; ACYLATION; DIACETYL; DFT; TRIFLUOROMETHYLATION; QUINOXALINES; DERIVATIVES;

D O I：

10.1021/acs.joc.0c01203

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition metal- and oxidant-free visible light-photoinduced protocol for direct functionalization of 2-methylquinolines has been developed. This protocol enabled the C-H functionalization of substituted 2-methylquinolines with diacetyl or ethyl pyruvate, under environmentally friendly conditions. A mechanistic investigation based on density functional theory (DFT) calculations provided details about the origins of reactivity and selectivity.

引用

页码：11663 / 11678

页数：16

共 77 条

[1] An efficient one-pot strategy for the highly regioselective metal-free synthesis of 1,4-disubstituted-1,2,3-triazoles [J].

Ali, Akbar ;

Correa, Arlene G. ;

Alves, Diego ;

Zukerman-Schpector, Julio ;

Westermann, Bernhard ;

Ferreira, Marco A. B. ;

Paixao, Marcio W. .

CHEMICAL COMMUNICATIONS, 2014, 50 (80) :11926-11929

[2] Relationships between step and cumulative PMI and E-factors: implications on estimating material efficiency with respect to charting synthesis optimization strategies [J].

Andraos, John .

GREEN PROCESSING AND SYNTHESIS, 2019, 8 (01) :324-336

[3]

Bally T, 1999, REV COMP CH, V13, P1, DOI 10.1002/9780470125908.ch1

[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] Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™ [J].

Bousfield, Thomas W. ;

Pearce, Katharine P. R. ;

Nyamini, Simbarashe B. ;

Angelis-Dimakis, Athanasios ;

Camp, Jason E. .

GREEN CHEMISTRY, 2019, 21 (13) :3675-3681

[6] Visible light-mediated C-P bond formation reactions [J].

Cai, Bao-Gui ;

Xuan, Jun ;

Xiao, Wen-Jing .

SCIENCE BULLETIN, 2019, 64 (05) :337-350

[7] Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis [J].

Capaldo, Luca ;

Ravelli, Davide .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) :2056-2071

[8] High throughput one pot synthesis of 2-methylquinolines [J].

Chandrashekarappa, Kiran Kumar H. ;

Mahadevan, Kittappa M. ;

Manjappa, Kiran B. .

TETRAHEDRON LETTERS, 2013, 54 (11) :1368-1370

[9] Metal-free decarboxylative acylation of isoquinolines using α-keto acids in water [J].

Chaubey, Narendra R. ;

Singh, Krishna Nand .

TETRAHEDRON LETTERS, 2017, 58 (24) :2347-2350

[10] Photoinduced reduction of water by diacetyl [J].

Coelhan, M ;

Parlar, H .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2001, 144 (2-3) :153-157

← 1 2 3 4 5 6 7 8 →