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[1,4]-Aza-Brook Rearrangement for Efficient Formation of Benzynes and Their Cycloaddition
Huang, ZA (Huang, Ze-Ao)1; Tang, F (Tang, Fan)1; Xu, YJ (Xu, Yan-Jun)1; Lu, CD (Lu, Chong-Dao)1; Lu, CD
2015
Source PublicationSYNLETT
Volume26Issue:7Pages:891-896
AbstractAn efficient benzyne cycloaddition triggered by an aza-Brook rearrangement is reported. In this reaction, 2-(trimethylsilyl)aryl triflates bearing a benzylic secondary amine group at the 3-position undergo base-promoted [1,4]-carbon-to-nitrogen silyl migration (aza-Brook rearrangement) to generate benzyne intermediates, which are then trapped by intermolecular or intramolecular cycloaddition involving 1,3-dienes or 1,3-dipoles. This procedure furnishes various cycloadducts in yields of up to 99%.
KeywordSilyl Migration Amines Aza-brook Rearrangement Benzyne Cycloaddition
DOI10.1055/s-0034-1380187
Indexed BySCI
WOS IDWOS:000352796300005
Citation statistics
Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/4909
Collection省部共建新疆特有药用资源利用重点实验室
Corresponding AuthorLu, CD
Affiliation1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zones, Urumqi 830011, Peoples R China
2.Chinese Acad Sci, Univ Chinese Acad Sci, Urumqi 830011, Peoples R China
3.Changji Univ, Dept Chem & Appl Chem, Changji 831100, Peoples R China
Recommended Citation
GB/T 7714
Huang, ZA ,Tang, F ,Xu, YJ ,et al. [1,4]-Aza-Brook Rearrangement for Efficient Formation of Benzynes and Their Cycloaddition[J]. SYNLETT,2015,26(7):891-896.
APA Huang, ZA ,Tang, F ,Xu, YJ ,Lu, CD ,&Lu, CD.(2015).[1,4]-Aza-Brook Rearrangement for Efficient Formation of Benzynes and Their Cycloaddition.SYNLETT,26(7),891-896.
MLA Huang, ZA ,et al."[1,4]-Aza-Brook Rearrangement for Efficient Formation of Benzynes and Their Cycloaddition".SYNLETT 26.7(2015):891-896.
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