1315477-86-1

Basic information

• Product Name: (E)-2-(iodomethylene)-3-phenyl-1-tosyl-2,3-dihydro-1H-benzo[f]indol-3-ol
• Synonyms: (E)-2-(iodomethylene)-3-phenyl-1-tosyl-2,3-dihydro-1H-benzo[f]indol-3-ol
• CAS NO: 1315477-86-1
• Molecular Weight: 553.42
• Mol File: 1315477-86-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-2-(iodomethylene)-3-phenyl-1-tosyl-2,3-dihydro-1H-benzo[f]indol-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(iodomethylene)-3-phenyl-1-tosyl-2,3-dihydro-1H-benzo[f]indol-3-ol(1315477-86-1)
• EPA Substance Registry System: (E)-2-(iodomethylene)-3-phenyl-1-tosyl-2,3-dihydro-1H-benzo[f]indol-3-ol(1315477-86-1)

Safety Data

• Hazardous Substances Data: 1315477-86-1(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 55270-95-6 (3-aminonaphthalen-2-yl)(phenyl)methanone 
• 1315477-46-3 1-phenyl-1-(2-(tosylamino)naphthalen-3-yl)prop-2-yn-1-ol 

Relevant articles and documents

Gold-catalyzed cycloisomerizations of 1-(2-(Tosylamino)phenyl)prop-2-yn-1- ols to 1H-Indole-2-carbaldehydes and (E)-2-(Iodomethylene)Indolin-3-ols

A method to prepare lH-indole-2-carbaldehydes and (E)-2-(iodomethylene) indolin-3-ols by gold(I)-catalyzed cycloisomerization of l-(2-(tosylamino) phenyl)prop-2-yn-1-ols with N-iodosuccinimide (NIS) is reported. The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in good to excellent yields (70-99%). The mechanism is suggested to involve activation of the alkyne moiety of the substrate by the gold(I) catalyst. This triggers intramolecular addition of the tethered aniline moiety to give a vinyl gold intermediate, which undergoes iododeauration with NIS to give the (E)-2-(iodomethylene)indolin-3-ol adduct. Subsequent 1,3-allylic alcohol isomerization (1,3-AAI) followed by formylation of this vinyl iodide intermediate then gives the 1H-indole-2-carbaldehyde.