Divergent Coupling of 2-Aryl-1,3-Indandiones with Alkenes Enabled by Iodine Catalyst

被引：14

作者：

Shi, Yue ^{[1
]}

Wang, Di ^{[1
]}

Sun, Ruzhong ^{[1
]}

Chen, Xin ^{[1
]}

Xu, Xuefeng ^{[1
]}

Xie, Haiquan ^{[1
]}

Zhang, Xu ^{[1
]}

机构：

[1] Nanyang Normal Univ, Coll Chem & Pharmaceut Engn, Engn Technol Res Ctr Henan Prov Solar Catalysis, Nanyang 473061, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 05期

关键词：

2-Aryl-1; 3-Indandiones; Alkenes; Dimethyl Sulfoxide; Iodine Catalyst; SELECTIVE OXIDATION; METAL-FREE; RADICALS; 1,3-INDANDIONE; CONSTRUCTION; AGGREGATION; DERIVATIVES; ALCOHOLS; KETONES; SYSTEM;

D O I：

10.1002/adsc.202201365

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein, we report an iodine-catalyzed protocol for cross-coupling of 2-aryl-1,3-indandiones with alkenes. Divergent reactivity was achieved in the transformation by varying additives and solvents, thus allowing selective access to tertiary alkylated ketones and alkenes. The present approach features commercially available starting materials, broad substrate scope, general functional-group (including halogen, ester, nitrile, thioether) tolerance. Furthermore, we proposed plausible pathways to rationalize the divergent selectivity through preliminary mechanism study.

引用

页码：741 / 746

页数：6

共 44 条

[1] Amidi S, 2013, IRAN J PHARM RES, V12, P91
[2] [Anonymous], 2004, ANGEW CHEM, V116, P6709
[3] [Anonymous], 2016, ANGEW CHEM, V128, P1926
[4] [Anonymous], 2020, Angew. Chem, V132, P227
[5] The molecular diversity scope of 1,3-indandione in organic synthesis
Asadi, Shima
Ziarani, Ghodsi Mohammadi
[J]. MOLECULAR DIVERSITY, 2016, 20 (01) : 111 - 152
[6] Organic Dye-Catalyzed Intermolecular Radical Coupling of α-Bromocarbonyls with Olefins: Photocatalytic Synthesis of 1,4-Ketocarbonyls Using Air as an Oxidant
Chowdhury, Soumyadeep Roy
Singh, Deepak
Ul Hoque, Injamam
Maity, Soumitra
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21) : 13939 - 13950
[7] TBAI/TBHP-Promoted Generation of Malonyl Radicals: Oxidative Coupling with Styrenes Leads to γ-Keto Diesters
Chowdhury, Soumyadeep Roy
Ul Hoque, Injamam
Maity, Soumitra
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (19) : 2824 - 2828
[8] Indandione-Terminated Quinoids:Facile Synthesis by Alkoxide-Mediated Rearrangement Reaction and Semiconducting Properties
Du, Tian
Gao, Ruiheng
Deng, Yunfeng
Wang, Cheng
Zhou, Qian
Geng, Yanhou
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (01) : 221 - 225
[9] Enantioselective Syntheses of C2-Symmetric Pyrazolones and Diones via One-Pot Organo-/Iodine Sequential Catalysis
Feng, Kai-Xiang
Tang, Cheng-Ke
Shen, Qiao-Yu
Xia, Ai-Bao
Huang, Li-Sha
Zhou, Zhan-Yu
Zhang, Xing
Du, Xiao-Hua
Xu, Dan-Qian
[J]. ORGANIC LETTERS, 2021, 23 (17) : 6750 - 6755
[10] Transition-metal- and organic-solvent-free: a highly efficient anaerobic process for selective oxidation of alcohols to aldehydes and ketones in water
Gogoi, P
Konwar, D
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (19) : 3473 - 3475

← 1 2 3 4 5 →