38829-06-0

Upstream product

• 29128-15-2 acetic acid-(3-p-tolyl-but-3-enyl ester) 
• 624-31-7 4-tolyl iodide 
• 32657-89-9 1,3-butadien-2-ylmagnesium chloride 
• 122-00-9 para-methylacetophenone 
• 920299-65-6 1,2-epoxy-3-(p-tolyl)-3-butene 
• 623-73-4 diazoacetic acid ethyl ester 
• 6773-29-1 dimethyl diazomalonate 
• 33458-08-1 1-(1,2-dibromoethyl)-4-methylbenzene 
• 51270-89-4 1-(1-bromoethenyl)-4-methylbenzene 
• 75927-49-0 pinacol vinylboronate 
• 51431-59-5 2-(p-tolyl)but-3-en-2-ol 
• 1311260-04-4 tert-butyl (2-(p-tolyl)but-3-en-2-yl) carbonate 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 124740-02-9 2-chloroformyl-4-(4'-methylphenyl)-3,6-dihydro-1,2-oxazine 
• 124740-03-0 2-chloroformyl-5-(4'-methylphenyl)-3,6-dihydro-1,2-oxazine 
• 51431-62-0 1-(2,2-Dichloro-1-vinyl-cyclopropyl)-4-methyl-benzene 
• 51431-68-6 1-(2,2-Dichloro-1-ethyl-cyclopropyl)-4-methyl-benzene 
• 1573120-89-4 (E)-3-(4-methylphenyl)-1-phenyl-3-penten-1-one 
• 1367737-01-6 4-(4-methylphenyl)-2-phenyl-3,6-dihydro-2H-pyran 

Relevant academic research and scientific papers

A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin

Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleo phile for cross-coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels-Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

Intermolecular oxonium ylide mediated synthesis of medium-sized oxacycles

Detailed in this account are our efforts toward efficient oxacycle syntheses. Two complementary approaches are discussed, with both employing chemoselective allyl ether activation and rearrangement as the key step. Vinyl substituted oxiranes and oxetanes provide a single step access to dihydropyrans and tetrahydrooxepines. Oxiranes proved to be poor substrates, while oxetanes were slightly better. An alternative approach using substituted allyl ethers proved successful and addressed the limitations encountered in the ring expansions.

Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of racemic tertiary allylic carbonates and allylboronates is described. This reaction generates all-carbon quaternary centers in a highly regioselective and enantioselective fashion. The outcome of these reactions is consistent with a process that proceeds by way of 3,3′-reductive elimination of bis(η1-allyl)palladium intermediates. Strategies for distinguishing the product alkenes and application to the synthesis of (+)-α-cuparenone are also described.

Synthesis of 2-Substituted 1,3-Butadienes by Cross-coupling Reaction of 2-(1,3-Butadienyl)magnesium Chloride with Alkyl or Aryl Iodides

The cross-coupling reactions of 2-(1,3-butadienyl)magnesium chloride (1) with aryl and alkyl iodides were investigated in the presence of transition metal catalysts.Tetrakis(triphenylphosphine)palladium(0) catalyzes the cross-coupling reactions of 1 with