79211-50-0

Upstream product

• 124745-26-2 4-<(1-methyl-3-(4-methylphenyl)prop-2-enyl)sulfinyl>morpholine 
• 86739-16-4 <((E)-But-2-enyl)oxy>trimethylsilan 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 104-81-4 4-Methylbenzyl bromide 
• 20574-99-6 1-(but-3-en-1-yl)-4-methylbenzene 
• 1106964-40-2 1-methylprop-2-ene-1-sulfonyl chloride 
• 106-99-0 buta-1,3-diene 
• 108-88-3 toluene 

Relevant academic research and scientific papers

METHODS OF BORYLATION AND USES THEREOF

The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.

Iron-Catalyzed Tunable and Site-Selective Olefin Transposition

The catalytic isomerization of C-C double bonds is an indispensable chemical transformation used to deliver higher-value analogues and has important utility in the chemical industry. Notwithstanding the advances reported in this field, there is compelling demand for a general catalytic solution that enables precise control of the C═C bond migration position, in both cyclic and acyclic systems, to furnish disubstituted and trisubstituted alkenes. Here, we show that catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound, promote efficient and controllable alkene transposition. Mechanistic investigations reveal that these processes likely involve in situ formation of an iron-hydride species which promotes olefin isomerization through sequential olefin insertion/β-hydride elimination. Through this strategy, regiodivergent access to different products from one substrate can be facilitated, isomeric olefin mixtures commonly found in petroleum-derived feedstock can be transformed to a single alkene product, and unsaturated moieties embedded within linear and heterocyclic biologically active entities can be obtained.

Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis

We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.

Ligandless iron-catalyzed desulfinylative C-C allylation reactions using Grignard reagents and alk-2-enesulfonyl chlorides

Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard reagents (aromatic, aliphatic, and heteroaromatic). The reaction can be catalyzed with even 2 mol-% of the simple iron salt Fe(acac)3. The regioselectivity of these allylations was studied by using sulfonyl chlorides 3 and 4 with aryl Grignard reagents. The scope of these allylations was further extended by the coupling of ester-substituted alk-2-enesulfonyl chloride 10 with aromatic Grignard reagents. Symmetrical products were synthesized by double C-C allylation with the use of 2-methylidenepropane-1,3-disulfonyl chloride (12). Wiley-VCH Verlag GmbH & Co. KGaA.

Hydrogen peroxide-or sodium hypochlorite-induced bromination of 1-arylbut-2-enes

Bromination of 1-arylbut-2-enes in the system [HBr or NaBr (KBr)-HX]-H 2O2 (or NaOCl) under relatively mild conditions leads to electrophilic addition of bromine or hypobromous acid at the side-chain double bond. Under more severe conditions, the process is accompanied by bromination of the aromatic ring. Treatment of the title compounds with peroxy acids (RCOOH-H2O2) gives the corresponding epoxy derivatives which react with HBr and oxygen-containing nucleophiles to produce α-bromo alcohols, diols, and diol acetates.

STEREOSELECTIUVE FORMATION OF (E)-OLEFINS HYDROLYTIC DESULPHINYLATION OF SOME SUBSTITUTED 4-(2'-ALKENESULPHINYL)-MORPHOLINES

The boron trifluoride-etherate catalysed hydrolysis of the title sulphinamides 1 provide olefins with (E:Z)-ratios depending on the nature of the substituents on the allylic chain.

REGIO- AND STEREO-CHEMISTRY IN ALLYLATION OF ARYL GRINARD REAGENTS CATALYZED BY PHOSPHINE-NICKEL AND -PALLADIUM COMPLEXES

Nickel and palladium complexes with the 1,1'-bis(diphenylphosphino)ferrocene ligand effectively catalyze regioselective cross-coupling of allylic ethers such as 1- or 3-methyl-2-propenyl silyl ethers with aryl-Grinard reagents, where the nickel catalyst l