19988-49-9

Upstream product

• 121730-98-1 4,4-diphenyl-2-isopropyl-3-butenal 
• 1350911-35-1 (Z)-1-phenylprop-1-enyl methylphenylcarbamate 
• 1888-75-1 isopropyllithium 
• 93-55-0 1-phenyl-propan-1-one 
• 119-61-9 benzophenone 
• 28322-40-9 isoamyltriphenylphosphonium bromide 
• 78-77-3 Isobutyl bromide 
• 26189-62-8 phenyl 2,2-diphenylethenyl sulfone 
• 74-85-1 ethene 
• 75-29-6 isopropyl chloride 
• 107-82-4 i-pentyl bromide 
• 2050-07-9 4-methyl-1-phenylpentan-1-one 

Relevant academic research and scientific papers

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Alkenylation of unactivated alkyl bromides through visible light photocatalysis

Two visible-light driven alkenylation reactions of unactivated alkyl bromides, which were enabled by the use of Ir(dF(CF3)ppy)2(dtbbpy)PF6 as the photocatalyst and (TMS)3SiH as the atom transfer reagent to activate the alkyl bromides, were described for the first time. These protocols can be used to produce a variety of alkenes from easily available feedstock with good reaction efficiency and high chemoselectivity under mild reaction conditions. To further demonstrate the applicability of the present strategy, the alkenylation of bioactive molecules and glycosyl bromides, as well as the alkynylation of unactivated alkyl bromides, was proven to be feasible.

Tertiary alcohols by tandem β-carbolithiation and N→C aryl migration in enol carbamates

Enol carbamates (O-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and bearing an N-aryl substituent undergo carbolithiation by nucleophilic attack at the (nominally nucleophilic) β position of the enol double bond. The resulting carbamate-stabilized allylic, propargylic, or benzylic organolithium rearranges with N→C migration of the N-aryl substituent, creating a quaternary carbon α to O. The products may be readily hydrolyzed to yield multiply branched tertiary alcohols in a one-pot tandem reaction, effectively a polarity-reversed nucleophilic β-alkylation-electrophilic α-arylation of an enol equivalent.

New results on the triplet photoreactivity of β,γ-unsaturated aldehydes: Diastereoselective synthesis of cyclopropanecarbaldehydes

A comparative study on the triplet photoreactivity of a series of β,γ-unsaturated aldehydes and methyl ketones has been carried out. Aldehydes 14 and 20 were found to undergo the oxa-di-π-methane rearrangement yielding the corresponding cyclopropane carbaldehydes 15 and 21 diastereoselectively. Decarbonylations and 1,3-carbonyl migrations have been observed in some cases, although these reactions do not take place via a Norrish Type I mechanism.