16692-57-2

Upstream product

• 502-56-7 nonanone-5 
• 6630-33-7 ortho-bromobenzaldehyde 
• 22949-84-4 butyl(triphenyl)phosphonium iodide 
• 693-04-9 butyl magnesium bromide 
• 643021-30-1 1-phenyl-5-(propane-1-sulfonyl)-1H-1,2,3,4-tetrazole 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 925-90-6 ethylmagnesium bromide 
• 124854-95-1 (E)-1-bromo-2-(3-bromoprop-1-en-1-yl)benzene 
• 3728-50-5 butylidenetriphenylphosphorane 

Downstream Products

• 16692-58-3 (E)-2-(pent-1-en-1-yl)benzoic acid 
• 1159683-89-2 C₁₁H₁₃I 
• 1373919-42-6 (E)-2-(pent-1-enyl) benzonitrile 
• 1438826-28-8 C₂₂H₃₉BO₃Si 
• 1438824-72-6 2-pentylphenyl dimethylsilane 
• 13397-96-1 1-bromo-2-pentylbenzene 
• 1162682-08-7 2-propyl-1-tosyl-1H-indole 
• 220903-35-5 (Z)-2-(pent-1-en-1-yl)benzaldehyde 
• 1342886-90-1 2-(2-bromophenyl)pentanal 
• 1342886-79-6 C₁₁H₁₄Br₂O 

Relevant academic research and scientific papers

Rhodium-catalyzed intramolecular hydroacylation of 1,2-disubstituted alkenes for the synthesis of 2-substituted indanones

The intramolecular hydroacylation of 1,2-disubstituted alkenes was considered to be a challenging task due to the side reactions resulted from the lack of additional substituent at 1-position and the low activity caused by the steric hindrance of substituent at 2-position, and an asymmetric version has not been considered possible due to problems associated with the racemization of the products. We have partially solved these problems. Catalyzed by an activated diphosphine-Rh complex and reacted in a selected dihalogenated solvent, the intramolecular hydroacylation of o-(2-arylvinyl)benzaldehydes provided the corresponding 2-aryl-1-indanones in high yields, and its asymmetric variant using o-(2-alkylvinyl)benzaldehydes afforded chiral 2-alkyl-1-indanones in high yields and with moderate enantioselectivities.

P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation

Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

ALKENES AS ALKYNE EQUIVALENTS IN RADICAL CASCADES TERMINATED BY FRAGMENTATIONS

Disclosed are methods for rerouting radical cascade cyclizations by using alkenes as alkyne equivalents. The reaction sequence is initiated by a novel 1,2 stannyl shift which achieves chemo- and regioselectivity in the process. The radical “hopping” leads to the formation of the radical center necessary for the sequence of selective cyclizations and fragmentations to follow. In the last step of the cascade, the elimination of a rationally designed radical leaving group via β-C—C bond scission aromatizes the product without the need for external oxidant. The Bu3Sn moiety, which is installed during the reaction sequence, allows further functionalization of the product via facile reactions with electrophiles as well as Stille and Suzuki cross-coupling reactions. This selective radical transformation opens a new approach for the controlled transformation of enynes into extended polycyclic structures of tunable dimensions.

Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents

A highly efficient method for the copper-catalyzed asymmetric allylic alkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr·SMe2 and TaniaPhos as chiral ligands gives

Design of leaving groups in radical C-C fragmentations: Through-bond 2c-3e interactions in self-terminating radical cascades

Radical cascades terminated by β-scission of exocyclic C-C bonds allow for the formation of aromatic products. Whereas β-scission is common for weaker bonds, achieving this reactivity for carbon-carbon bonds requires careful design of radical leaving groups. It has now been found that the energetic penalty for breaking a strong σ-bond can be compensated by the gain of aromaticity in the product and by the stabilizing two-center, three-electron "half-bond" present in the radical fragment. Furthermore, through-bond communication of a radical and a lone pair accelerates the fragmentation by selectively stabilizing the transition state. The stereoelectronic design of radical leaving groups leads to a new, convenient route to Sn-functionalized aromatics.

A SINGLE STEP ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF 3-SUBSTITUTED CHIRAL PHTHALIDES

The present invention discloses single step, highly enantioselective catalytic oxidative cyclization process for the synthesis of 3-substituted chiral phthalides. In particular, the invention discloses asymmetric synthesis of chiral phthalides via synergetic nitrile accelerated oxidative cyclization of o-cyano substituted aryl alkenes in high yield and enantiomeric excess (ee) in short reaction time. Also, disclosed herein is "one -pot" asymmetric synthesis of biologically important natural compounds having 3-substituted chiral phthalide structural framework in the molecule.

Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane

Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.

A visible-light-mediated oxidative C-N bond formation/aromatization cascade: Photocatalytic preparation of N-arylindoles

Just add light and air: Structurally diverse N-arylindoles can be prepared from readily prepared o-styryl anilines through visible-light photocatalysis. The reaction, which is conducted open to air, is mediated by [Ru(bpz) 3](PF6)2 (bpz=2,2'-bipyrazine) and involves both C-N bond formation and aromatization (see scheme). Using suitably substituted substrates, a 1,2-carbon shift can be also incorporated into this cascade reaction. Copyright

CN-assisted oxidative cyclization of cyano cinnamates and styrene derivatives: A facile entry to 3-substituted chiral phthalides

The asymmetric dihydroxylation (AD) of o-cyano cinnamates and styrene derivatives leads to efficient construction of chiral phthalide frameworks in high optical purities. This unique reaction is characterized by unusual synergism between CN and osmate groups resulting in rate enhancement of the AD process. The method is amply demonstrated by the synthesis and the structural/stereochemical assignment of the natural products.

Alkenyl substituted bicyclic nucleoside analogues retain nanomolar potency against Varicella Zoster Virus

Novel alkenyl substituted aryl bicyclic furano pyrimidines have been prepared and evaluated in vitro against Varicella Zoster Virus (VZV). The para-substituted analogues retain the nanomolar potency we have reported for p-alkyl analogues, while the ortho-