![1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine structure](https://static.chemtradehub.com/structs/121/1218790-44-3-baef.webp "1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine structure")
1-{[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]methyl}piperidine
CAS Number:
1218790-44-3
Molecular Formula:
C16H26BNO2S
Highly selective synthesis of 6-substituted benzothiophenes by Sc(OTf)3-catalyzed intermolecular cyclization and sulfur migration
Literature Information
Publication Date
2016-09-12
DOI
10.1039/C6QO00477F
Impact Factor
5.281
Authors
Xiaoming Wang, Tobias Gensch, Frank Glorius
View Original
Abstract
A series of 6-substituted benzo[b]thiophenes was efficiently synthesized using a Sc(OTf)3-catalyzed intermolecular cyclization between para-substituted N-(arylthio)succinimides and alkynes taking advantage of a unique and selective 1,2-sulfur migration. Investigations with DFT shed light on the migration process occuring via an electrophilic ipso cyclization of a vinyl cation to a key spirocyclic thiete intermediate.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl (1-cyclobutyl-3-hydroxy-2-propanyl)carbamate
CAS Number:
816429-99-9
Molecular Formula:
C12H23NO3
![1-Oxa-8-azaspiro[4.5]decan-3-ol structure](https://static.chemtradehub.com/structs/757/757239-76-2-a0ec.webp "1-Oxa-8-azaspiro[4.5]decan-3-ol structure")
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