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Upstream product

• 118878-79-8 Dichlorneopentylsilaethen 
• 100-52-7 benzaldehyde 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 594-19-4 tert.-butyl lithium 
• 6852-56-8 N-benzylideneisopropylamine 
• 6852-58-0 N-benzylidene tert-butylamine 
• 538-51-2 benzylidene phenylamine 
• 622-29-7 N-Benzylidenemethylamine 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 1070-83-3 tert-Butylacetic acid 
• 1808-38-4 bis(tert-butylacetyl)peroxide 
• 15501-33-4 neopentyl iodide 
• 86429-21-2 2-(dibromoboryl)-4,4-dimethyl-1-phenyl-2-pentene 

Relevant academic research and scientific papers

Method for synthesizing cis-olefin by catalyzing decarboxylation coupling reaction of NHP ester and aryl-terminated alkyne with iridium

The invention provides a method for synthesizing Z-selective olefin by catalyzing a decarboxylation coupling reaction of an NHP ester and aryl-terminated alkyne with iridium. The aryl-terminated alkyne and its derivative and the NHP ester undergo a one-po

Selective Syntheses of Z-Alkenes via Photocatalyzed Decarboxylative Coupling of N-Hydroxyphthalimide Esters with Terminal Arylalkynes

A novel, efficient Z-alkene synthesis via photocatalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as α-amino acid and α-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions, broad substrate scope, functional group tolerance, and operational simplicity make this decarboxylative coupling reaction a valuable method in organic syntheses.

Photo-induced Decarboxylative Heck-Type Coupling of Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of Sacrificial Hydrogen Acceptors

1,2-Disubstituted alkenes such as vinyl arenes, vinyl silanes, and vinyl boronates are among the most versatile building blocks that can be found in every sector of chemical science. We herein report a noble-metal-free method of accessing such olefins through a photo-induced decarboxylative Heck-type coupling using alkyl carboxylic acids, one of the most ubiquitous building blocks, as the feedstocks. This transformation was achieved in the absence of external oxidants through the synergistic combination of an organo photo-redox catalyst and a cobaloxime catalyst, with H2 and CO2 as the only byproducts. Both control experiments and DFT calculations supported a radical-based mechanism, which eventually led to the development of a selective three-component coupling of aliphatic carboxylic acids, acrylates, and vinyl arenes. More than 90 olefins across a wide range of functionalities were effectively synthesized with this simple protocol.

Hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides

A photo and nickel co-catalyzed hydroalkylation of terminal aryl alkynes enabled Z-preferred olefin synthesis has been developed under mild conditions. Alkyl diacyl peroxides were utilized as a new type of alkylation reagents and afforded Z-olefins as the major products in moderate to good yields.

Palladium-catalyzed intermolecular Heck reaction of alkyl halides

Intermolecular Heck reaction of common alkyl halides, a longstanding problem in palladium catalysis, is realized with a simple Pd/dppf catalyst. Both primary and secondary alkyl halides are suitable for coupling with aromatic olefins. Single electron transfer from (dppf)Pd0 to alkyl halide initiated the catalytic cycle and gave alkyl radicals. This journal is the Partner Organisations 2014.

Silaheterocycles, XXIII. - Synthesis and Thermolysis Reactions of Si-Functionalized 2-Silaazetidines

Dichloroneopentylsilene (1) is formed in situ by the reaction of trichlorovinylsilane with LitBu.The cycloaddition to imines yields Si,Si-dichloro-functionalized 2-silaazetidines in a preparative scale.With aldimines as trapping agents for 1, the resulting SiN four-membered ring compounds are isolated as syn/anti-isomers (e.g. syn/anti-15 and -16; syn/anti ca. 2:1).Silene 1 is not liberated from the silaazetidines on heating, but the Si,Si-dichloro-substituted silanimine Cl2Si=NtBu (24) is formed.This can be trapped by Me3SiOMe or Ph2C=NtBu to give the addition products 25 and 26, respectively.The pathways are discussed which lead to stereoisomeric SiN ring compounds by a multiple-step mechanism including zwitterionic intermediates (1,4-dipoles).In addition there is strong evidence for the formation of 1, depending on the trapping reagent used.This fact may be explained by donor->silene interactions.The thermolysis products of silaazetidines support the formulation of a stepwise decomposition to an alkene and Cl2Si=NR derivatives. Key Words: Silene, dichloroneopentyl- / Imines / Cycloaddition reactions / 2-Silaazetidines / Thermolysis reactions

Silaheterocycles VII; Reactions of Dichloroneopentylsilene with Aldehydes

Dichloroneopentylsilene, Cl2Si=CHCH2But (1), is produced from vinyltrichlorsilane (2) and LiBut in n-pentane at -78 deg C.The reactions of 1 with aromatic aldehydes like benzaldehyde and the 4-methoxy- or 4-fluoro-substituted derivatives, naphthalene-1 and -2- and 9-anthracenecarbaldehyde, furfurale and its S-analogous thiophene carbaldehyde yield 1,2-silaoxetanes by cycloaddition with the carbonyl group.The same is true for the reactions of 1 with pivaline-, butyr- and acetaldehyde.The silaoxetanes cannot be isolated; the formation of dichlorovinylsiloxanes and the olefinic compounds R-CH=CH-CH2But suggests that the cycloreversion of the Si-O four-membered ring competes with an intramolecular isomerization, evidently via formation of a zwitterionic intermediate R-C+HOSiCl2C-HCH2But.The product formation by coupling reactions of lithiated aldehydes and 2 is excluded by performing analogous reactions with the chlorosilanes Me2SiCl(R) (R=Cl, Me, Vi).

Boration Reactions with 1-Alkynes

Halodiorganoboranes R2BHal(R = Et, Ph) as well as benzyldihaloboranes PhCH2BHal2 undergo a regiospecific addition to the triple-bond of 1-alkynes ACCR'.The reversible haloboration (1) gives Z-alkenes as the more stable isomers.At elevated temperatures, the irreversible 1,1-organoboration (2) predominates, accompanied by a 1,2-transfer of A, whereas the 1,2-organoboration (3) is observed only as an unimportant side-reaction in a few cases.The cyclisation (4) occurs as a sequence of cis-haloboration and intramolecular aromatic alkenylation in the case of PhCH2BCl2 as borating agent.