23970-90-3

Upstream product

• 2048-31-9 (Z)-2-bromo-3-phenylprop-2-en-1-ol 
• 96725-18-7 2-bromo-1-phenyl-2-propen-1-ol 
• 2327-99-3 1-phenylpropadiene 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 100-42-5 styrene 
• 100-52-7 benzaldehyde 
• 59106-33-1 (Z)-ethyl 2-bromo-3-phenylprop-2-enoate 
• 23970-90-3 (Z)-(2,3-dibromoprop-1-en-1-yl)benzene 
• 96725-16-5 3-acetoxy-2-bromo-3-phenyl-1-propene 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 66820-54-0 β-bromocinnamyl alcohol 
• 5443-49-2 α-bromocinnamaldehyde 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 142334-87-0 [(Z)-2-Bromo-3-(2-methylene-cyclopentyl)-propenyl]-benzene 
• 353454-88-3 (Z)-1-(2-bromo-3-phenylprop-2-enyl)-6-oxo-1,6-dihydropyridine-2-carbonitrile 
• 1254219-13-0 diethyl 2-allyl-2-((Z)-3-phenyl-2-bromo-2-propenyl)malonate 
• 1254219-18-5 diethyl 2-(but-3-enyl)-2-((Z)-3-phenyl-2-bromo-2-propenyl)malonate 
• 1254219-15-2 N-allyl-N-((Z)-3-phenyl-2-bromo-2-propenyl)-p-toluenesulfonamide 
• 21003-54-3 (E)-(2,3-dibromoprop-1-enyl)benzene 
• 1254219-20-9 N-(but-3-enyl)-N-((Z)-3-phenyl-2-bromo-2-propenyl)-p-toluenesulfonamide 
• 1254219-21-0 N-(1-phenylbut-3-enyl)-N-((Z)-3-phenyl-2-bromo-2-propenyl)-p-toluenesulfonamide 
• 1254219-25-4 N-(1-phenylpent-4-enyl)-N-((Z)-3-phenyl-2-bromo-2-propenyl)-p-toluenesulfonamide 
• 1254219-30-1 C₃₃H₃₂BrNO₂S 

Relevant academic research and scientific papers

Transition metal-free diastereospecific synthesis of (Z)-2-arylidene-2,3-dihydrobenzo[b][1,4]dioxines by reaction of (Z)-1,2-dibromo-3-aryl-2-propenes with catechols

A transition metal-free, diastereospecific reaction between substituted (Z)-1,2-dibromo-3-phenyl-2-propenes and substituted catechols using Cs2CO3 as a base at 140 °C for 18 h delivers exclusively substituted (Z)-2-arylidene-2,3-dihy

Hydrodebromination of allylic and benzylic bromides with water catalyzed by a rhodium porphyrin complex

Hydrodebromination of allylic and benzylic bromides was successfully achieved by a rhodium porphyrin complex catalyst using water as the hydrogen source without a sacrificial reductant. Mechanistic investigations suggest that bromine atom abstraction via a rhodium porphyrin metalloradical operates to give the rhodium porphyrin alkyl species and the subsequent hydrolysis of the rhodium porphyrin alkyl species to a hydrocarbon product is a key step to harness the hydrogen from water.

Titanocene(III) chloride mediated radical induced addition-elimination route to the synthesis of racemic and optically active trisubstituted tetrahydrofurans: Formal synthesis of magnofargesin and 7’-epimagnofargesin

Titanocene(III) Chloride mediated radical induced synthesis of 4-benzylidene substituted tetrahydrofuran, a typical lignan skeleton, has been accomplished in good yield through addition-elimination route in racemic as well as in optically active forms. The method has been applied to the synthesis of furano lignans, magnofargesin (1) and 7’-epimagnofargesin (2) in optically active forms.

Selectfluor-mediated mild oxidative halogenation and thiocyanation of 1-aryl-allenes with TMSX (X = Cl, Br, I, NCS) and NH4SCN

Presence of TMSX (X = Cl, Br, I) unleashes the oxidative character of Selectfluor and provides a mild dihalogenation method for 1-arylallenes. Preference for 2,3-addition was observed with TMSCl in MeCN irrespective of the nature of the substituent on the aryl moiety, whereas 1,2-addition was preferred in [BMIM][BF4]. With TMSBr and TMSI only products corresponding to 2,3-addition were observed. Reactions carried out with TMSBr in IL solvents gave the corresponding monobromoalkenes as a major product along with the isomeric dibromo-alkenes. Reaction with NH4SCN provided convenient access to dithiocyanate derivatives. The same products were formed via TMS-NCS/Selectfluor. Formation of common products via TMSNCS and NH 4SCN points to the formation and interplay of SCN+/ NCS+ as incipient electrophiles.

2,3-dihalo-1-propenes as building blocks in Cu(I)-catalyzed domino reactions: Efficient and selective synthesis of furans

The Cu(I)-catalyzed reaction of 2,3-dibromo-1-propenes with β-ketoesters and 1,3-diketones, respectively, in DMF at 120 °C using Cs2CO3 as a base and hydroquinone as an additive exclusively delivers 2,3,5-trisubstituted furans and related compounds with yields up to 96%. The highly regioselective domino process is based on an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.

Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers

A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups. Copyright

Copper-free asymmetric allylic alkylation using grignard reagents on bifunctional allylic bromides

A series of substrates containing a vinylic bromide were employed in a copper-free methodology using bidendate NHC ligands. The desired compounds are generally obtained with good enantioselectivity and good regioselectivity. Importantly the copper-catalyzed system afforded a lower enantioselectivity value. The catalytic products could be transformed into a broad scope of new 1,1-disubstituted olefins in a single step transformation without erosion of the enantioselectivity.

Efficient ring-closing metathesis of alkenyl bromides: The importance of protecting the catalyst during the olefin approach

We present the first productive ring-closing metathesis reaction that leads to the construction of cyclic alkenyl bromides. Efficient catalysis employing commercially available Grubbs II catalyst is possible through appropriate modification of the starting bromoalkene moiety.

Conversion of bromoalkenes into alkynes by wet tetra-n-butylammonium fluoride

(Chemical Equation Presented) Tetra-n-butylammonium fluoride was found to be a mild and efficient base for the elimination reaction of bromoalkenes. Treatment of 1,1-dibromoalkenes, (Z)-1-bromoalkenes, and internal bromoalkenes with 5 equiv of TBAF·3H2O in DMF yielded terminal and internal alkynes in high yields without undue regard to the presence of water.

Cascade radical synthesis of heteroarenes via iminyl radicals

A novel cascade cyclisation protocol has been developed which 'zips up' two rings to form new tetracycles. In the protocol, treatment of vinyl bromides and iodides with hexamethylditin (Me3Sn· yields intermediate vinyl radicals which undergo 5-exo cyclisation onto nitrile groups to yield intermediate iminyl radicals. The iminyl radicals can undergo 6-endo cyclisation (or 5-exo followed by neophyl rearrangement) to yield tetracyclic π-radicals which lose hydrogen (H·) in an H-abstraction step. Methyl radicals, generated from the breakdown of trimethylstannyl radicals (Me3Sn·), are proposed as a possible H-abstractor for this final oxidative step. The protocol has been used to synthesise the tetracyclic rings A-D (tetracycle indolizino[1,2-b]quinolin-9(11H)-one) of the anticancer alkaloids camptothecin, mappicine, nothapodytine B and nothapodytine A. The protocol has also been applied to the synthesis of analogues of camptothecin in which ring A has been replaced by thiophene (8,10-dihydrothieno[2′,3′:5,6]pyrido[2,3-a]indolizin-8-one) and ring D by pyrrole (10H-pyrrolizino[1,2-b]quinoline) and benzene (11H-indeno[1,2-b]quinolin-11-one).