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Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols
Ma, Shuang-Shuang1,2; Sun, Rui1,2; Zhang, Zi-Heng1,3; Yu, Zheng-Kun4; Xu, Bao-Hua1,2,4
2021-10-13
Source PublicationORGANIC CHEMISTRY FRONTIERS
ISSN2052-4129
Pages10
AbstractThe alkylation of nitroarenes with alkanols catalysed by a phosphinesulfonate chelated ruthenium complex [Ru-1] was developed. It exhibits very different reactivity and chemoselectivity depending on acidic-basic conditions. Under either neutral or acidic conditions, nitroarenes were converted to secondary and tertiary anilines, respectively, with secondary and primary alkanols. By contrast, the same catalyst promotes the N-monoalkylation of nitroarenes with primary alkanols under alkaline conditions, while both N-monoalkylation with secondary alkanols and N-dialkylation with primary alkanols are inhibited. Mechanistic studies demonstrated that the novel reactivity under alkaline-free conditions is attributed to the sulfonate ligand-assisted O-H activation of alkanols, thus enabling the reduction of nitroarenes and nucleophilic C-N coupling in a concerted approach. Furthermore, it follows the traditional two-step approach, taking the corresponding imines as the intermediates, under alkaline conditions. Based on such features, diverse secondary and tertiary anilines were obtained directly from nitroarenes using the same catalyst [Ru-1].
DOI10.1039/d1qo01269j
Language英语
WOS KeywordREDUCTIVE N-ALKYLATION ; H BOND ACTIVATION ; NITRO-COMPOUNDS ; BORONIC ACIDS ; ELECTROPHILIC AMINATION ; COOPERATIVE CATALYSIS ; SECONDARY-AMINES ; BRONSTED ACID ; ALCOHOLS ; LIGANDS
Funding ProjectExcellent Young Scientists Fund[22022815] ; Innovation Academy for Green Manufacture, CAS[IAGM2020C13] ; Zhengzhou High Level Talent Certificate[20180200052] ; K. C. Wong Education Foundation[GJTD-2018-04]
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationExcellent Young Scientists Fund ; Innovation Academy for Green Manufacture, CAS ; Zhengzhou High Level Talent Certificate ; K. C. Wong Education Foundation
WOS IDWOS:000712551200001
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/50831
Collection中国科学院过程工程研究所
Corresponding AuthorXu, Bao-Hua
Affiliation1.Chinese Acad Sci, Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Sch Chem & Chem Engn, Beijing 100049, Peoples R China
3.Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China
4.Chinese Acad Sci, Innovat Acad Green Manufacture, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Ma, Shuang-Shuang,Sun, Rui,Zhang, Zi-Heng,et al. Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols[J]. ORGANIC CHEMISTRY FRONTIERS,2021:10.
APA Ma, Shuang-Shuang,Sun, Rui,Zhang, Zi-Heng,Yu, Zheng-Kun,&Xu, Bao-Hua.(2021).Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols.ORGANIC CHEMISTRY FRONTIERS,10.
MLA Ma, Shuang-Shuang,et al."Ruthenium-catalysed chemoselective alkytation of nitroarenes with alkanols".ORGANIC CHEMISTRY FRONTIERS (2021):10.
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