87587-40-4

Upstream product

• 87587-24-4 N-benzyl-2-(hex-1-yn-1-yl)aniline 
• 142272-83-1 1-chloro-2-(hex-1-yn-1-yl)benzene 
• 100-46-9 benzylamine 
• 693-02-7 hex-1-yne 
• 76464-99-8 N-benzyl-2-iodoaniline 
• 615-43-0 2-iodophenylamine 
• 116491-50-0 2-(hex-1-ynyl)aniline 
• 87587-23-3 N-benzyl-N-phenyl-O-(trimethylsilyl)hydroxylamine 

Relevant academic research and scientific papers

Synthesis and Catalytic Activity of Coumarin- and Chrysin-Tethered Triazolylidene Gold(I) Complexes

A series sterically-encumbered coumarin- (1) and chrysin-functionalized triazolium salts (2,3) have been synthesized stepwise via copper catalyzed alkyne–azide cycloaddition and N-alkylation procedures. Their one-pot deprotonation with KHMDS in presence of AuCl(SMe2) allowed for the preparation of the corresponding triazolylidene gold(I) complexes (4–6) in high yields (75–92 %). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, FT-IR, elemental analyses and in the case of triazole F, triazolium 1 and the gold complex 4, by single-crystal X-ray diffraction. The new triazolylidene gold complexes (4–6) were tested as precatalysts in the synthesis of indole derivatives via an intramolecular hydroamination reaction of several readily available anilines.

Borane-catalyzed indole synthesis through intramolecular hydroamination

The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline 8 in good yield.

Simple and Mild Synthesis of Indoles via Hydroamination Reaction Catalysed by NHC-Gold Complexes: Looking for Optimized Conditions

An efficient heterocyclization of 2-alkynylanilines to indole derivatives has been developed. The reaction proceeds under very mild conditions using small amounts of a gold precatalyst. A range of substrates possessing various functional groups were employed, and the substituted indoles were obtained in very good yields.

Simple indole synthesis by one-pot sonogashira coupling-NaOH-mediated cyclization

Coupling of o-iodoanilines with terminal alkynes under standard Sonogashira conditions, and further treatment with NaOH under conventional heating or microwave irradiation, afford 2-substituted indoles in usually high yields. Functionalities such as halides, nitro, and cyano groups are tolerated under the reaction conditions. Georg Thieme Verlag Stuttgart.

2,3-Disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole

A metalative 5-endo-dig cyclization reaction of 2-ynylphenoles or anilines effected by BuLi and ZnCl2 produces 3-zinciobenzoheteroles in excellent yield. These intermediates have been transmetalated to the corresponding cuprates and allowed to react with electrophiles to produce a variety of 2,3-disubstituted benzofurans and indoles.

Efficient synthesis of 2-substituted indoles based on palladium(II) acetate/tri-tert-butylphosphine-catalyzed alkynylation/amination of 1,2-dihalobenzenes

A simple, efficient palladium(II) acetate/tri-tert-butylphosphine-catalyzed indole synthesis from o-alkynylhalobenzenes, readily available from 1,2-dihalobenzenes, has been achieved in good to excellent yields. A one-pot, Pd(OAc)2/t-Bu3P-catalyzed sequential reaction from 1-chloro-2-iodobenzene, phenylacetylene and amines has also been achieved in good yields.