DDQ-catalyzed oxidative α-allylation of isochromans under aerobic conditions

被引：0

作者：

Lee, Sujin ^{[1
,2
]}

Jung, Sunhwa ^{[1
,2
]}

Hyeon, Suyeon ^{[1
]}

Kim, Kyungmin ^{[1
,2
]}

Min, Sun-Joon ^{[1
,2
,3
]}

机构：

[1] Hanyang Univ, Dept Appl Chem, Ansan 15588, Gyeonggi Do, South Korea

[2] Hanyang Univ, Ctr Bionano Intelligence Educ & Res, Ansan 15588, Gyeonggi Do, South Korea

[3] Hanyang Univ, Dept Chem & Mol Engn, Ansan 15588, Gyeonggi Do, South Korea

来源：

RSC ADVANCES | 2024年 / 14卷 / 53期

关键词：

PICTET-SPENGLER CYCLIZATION; BENZYLIC ETHERS; BOND ARYLATION; ALKYLATION; ACID; ALKYNYLATION; ALDEHYDES; ADDITIONS; VERSATILE;

D O I：

10.1039/d4ra07586b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The allylation of isochromans at the alpha-position via aerobic DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) catalysis is described. This process involves the DDQ oxidation of various isochromans under mild conditions to generate oxocarbenium intermediates, which are effectively stabilized in equilibration in the presence of acid before undergoing allylation. Molecular oxygen and tert-butyl nitrite are employed as an environmentally benign oxidant and mediator, respectively, in the catalytic cycle. The transformation of an allylated product to biologically active molecules has also been successfully demonstrated.

引用

页码：39645 / 39652

页数：8

共 50 条

[41] Mild and efficient barbier allylation reaction mediated by magnesium powder under solvent-free conditions [J].

Li, Shunxi ;

Wang, Jin-Xian ;

Wen, Xiaoliu ;

Ma, Xiaofang .

TETRAHEDRON, 2011, 67 (05) :849-855

[42] Efficient CuOAc/DMAP/DEAD-Catalyzed Aerobic Oxidative Synthesis of Quinazolines [J].

Ji, Yue ;

Dang, Ze-Lin ;

Niu, Meng-Long ;

Gao, Qiang ;

Liu, Xuemei .

CHEMISTRYSELECT, 2024, 9 (39)

[43] Direct Synthesis of Amides from Coupling of Alcohols and Amines Catalyzed by Ruthenium(II) Thiocarboxamide Complexes under Aerobic Conditions [J].

Sindhuja, Elangovan ;

Ramesh, Rengan ;

Balaji, Sundarraman ;

Liu, Yu .

ORGANOMETALLICS, 2014, 33 (16) :4269-4278

[44] Palladium-Catalyzed Aerobic Oxidative Cross-Esterification of Aldehydes with Alcohols [J].

Gao, Meng ;

Chen, Meng ;

Li, Yang ;

Tang, Hong ;

Ding, Hao ;

Wang, Kai ;

Yang, Lingen ;

Li, Cuiting ;

Lei, Aiwen .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) :1566-1568

[45] Iron-catalyzed aerobic oxidative amidation of tertiary amines with carboxylic acids [J].

Ma, Lina ;

Li, Yuanming ;

Li, Zhiping .

SCIENCE CHINA-CHEMISTRY, 2015, 58 (08) :1310-1315

[46] Palladium-Catalyzed Aerobic Domino Oxidative Carbocyclization-Alkynylation of Allenynes [J].

Volla, Chandra M. R. ;

Backvall, Jan-E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :14209-14213

[47] Copper-catalyzed aerobic oxidative dicarbonylation of indoles utilizing α-carbonyl aldehydes [J].

Yang, Jin-Ming ;

Cai, Zhong-Jian ;

Wang, Qing-Dong ;

Fang, Dong ;

Ji, Shun-Jun .

TETRAHEDRON, 2015, 71 (38) :7010-7015

[48] Aerobic oxidative desulfurization of model mixtures under ultrasonic treatment [J].

Mingalev, P. G. ;

Kardashev, S. V. ;

Dudnik, V. D. ;

Lisichkin, G. V. .

RUSSIAN CHEMICAL BULLETIN, 2024, 73 (09) :2640-2645

[49] Facile Catalyst-Free Allylation of Isatins Under Mild Conditions in Dimethylformamide [J].

Jia, Li-Na ;

Peng, Lin ;

Wang, Liang-Liang ;

Bai, Jian-Fei ;

Fu, Ji-Ya ;

Huang, Qing-Chun ;

Wang, Fei-Ying ;

Xu, Xiao-Ying ;

Wang, Li-Xin .

LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (05) :352-357

[50] Aerobic Oxidative C(CO)-C Bond Cleavage under Catalyst-Free and Additive-Free Conditions [J].

Tian, Xinzhe ;

Ren, Yun-Lai ;

Cheng, Xinqiang ;

Lu, Weiwei .

CHEMISTRYSELECT, 2019, 4 (39) :11496-11499

← 1 2 3 4 5 →