19016-85-4

Upstream product

• 92078-65-4 (7-bromohept-1-yn-1-yl)benzene 
• 1119-51-3 bromopentene 
• 536-74-3 phenylacetylene 
• 57718-14-6 (7-iodohept-1-yn-1-yl)benzene 

Downstream Products

• 119639-64-4 2-phenylbicyclo<3.3.0>oct-1-en-3-one 
• 112399-67-4 (2,6-Dimethyl-phenyl)-[3-phenyl-4,5,6,6a-tetrahydro-1H-pentalen-(2E)-ylidene]-amine 
• 119639-69-9 1-((E)-(2-methylcyclopentylidiene)methyl)benzene 

Relevant academic research and scientific papers

Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates

We report a Ni-catalyzed diborylative cyclization of enynes that affords carbo- and heterocycles containing both alkyl- and alkenylboronates. The reaction is fully atom-economical, shows a broad scope, and employs a powerful and inexpensive catalytic Ni-b

Ni-Catalyzed Cyclization of Enynes and Alkynylboronates: Atom-Economical Synthesis of Boryl-1,4-dienes

We report a novel atom-economical Ni-catalyzed cyclization reaction of enynes with alkynylboronates. The reaction employs a non-expensive Ni salt, a phosphine-based ligand and easy-handling alkynylboronates as boron–carbon source. The reaction provides co

Iron-Catalyzed Hydroborylative Cyclization of 1,6-Enynes

We report first Fe-catalyzed hydroborylative cyclization reaction. The process provides one C?C and one C?B bond in a single operation and shows a wide scope, allowing the formation of carbo- and heterocycles containing a homoallylic boryl unit that can b

Ti-Catalyzed Multicomponent Oxidative Carboamination of Alkynes with Alkenes and Diazenes

The inter- or intramolecular oxidative carboamination of alkynes catalyzed by [py2TiCl2NPh]2 is reported. These multicomponent reactions couple alkenes, alkynes and diazenes to form either α,β-unsaturated imines or α-(iminomethyl)cyclopropanes via a TiII/TiIV redox cycle. Each of these products is formed from a common azatitanacyclohexene intermediate that undergoes either β-H elimination or α,γ-coupling, wherein the selectivity is under substrate control.

Catalytic reduction of phenyl-conjugated acetylenic halides by nickel(I) salen: Cyclization versus coupling

Cyclic voltammetry and controlled-potential electrolysis were employed to study the catalytic reduction of five phenyl-conjugated haloalkynes by nickel(I) salen electro-generated at carbon cathodes in dimethylformamide containing tetramethylammonium tetrafluoroborate. Electrocatalytic reduction of 7-bromo- and 7-iodo-1-phenyl-1-heptyne affords the carbocyclic product, benzylidenecyclohexane, in up to 41 % yield, whereas under similar conditions reduction of 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne gives benzylidenecyclobutane and benzylidenecycloheptane, respectively, in very low yield (≤1 %). Dimers, alkynes, and alkenynes are other products formed from the phenyl-conjugated haloalkynes. Dimers (diphenylalkadiynes) derived from 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne are obtained in yields ranging from 85 to 93 %, whereas 1,14-diphenyltetradeca-1,13-diyne (the dimer produced from 7-halo-1-phenyl-1-heptyne) is found in yields of 45-51 %. To account for the formation of the various products, a mechanistic scheme that involves phenyl-conjugated alkynyl radicals arising from nickel(I) salen catalyzed cleavage of the carbon-halogen bond of each substrate was formulated. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Novel decomplexation method for alkyne-Co2(CO)6 complexes

A novel and general decomplexation method for alkyne-Co2(CO)6 complexes has been established, which treats the complexes with ethylenediamine in THF.

Rate Enhancement of the Pauson-Khand Reaction by Primary Amines

Keywords: alkyne complexes; amines; carbonyl complexes; cobalt; cyclization

FREE RADICAL REARRANGEMENTS OF ORGANOCOBALOXIMES: ALKYNYL TO CYCLOALKYLIDENE AND HEXENYL TO CYCLOPENTYLMETHYL

Under irradiation by tungsten light in pyridine solution, several substituted alkylcobaloximes undergo rearrangement to more stable substituted alkyl- or alkenyl-cobaloximes.When the same reactions are carried out in the presence of carbon tetrachloride or chloroform, no rearranged organobaloximes are obtained, but a variety of organic products are obtained derived from the interception of transient organic radicals by the halogenated solvent.The rearrangements are rationalised in terms of a reversible homolysis of the carbon-cobalt bond, rearrangement of the organic radical and recapture by the cobalt(II) fragment to give complexes that are more stable to irradiation than their precursors.