A ligand-controlled regioselectivity switch of ring-opening coupling reaction of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents providing differently substituted β-vinylic naphthalenes in moderate to excellent yields was reported: when Pd(OAc)2 was used, the aromatic group from the Grignard reagent regioselectively coupled to the naphthyl ring after the ring-opening of three-me...

We describe an efficient continuous flow synthesis of ketones from CO2 and organolithium or Grignard reagents that exhibits significant advantages over conventional batch conditions in suppressing undesired symmetric ketone and tertiary alcohol byproducts. We observed an unprecedented solvent-dependence of the organolithium reactivity, the key factor in governing selectivity during the flow pro...

The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products ...

The possibility of generating MgH(2) nanoparticles from Grignard reagents was investigated. To this aim, five Grignard compounds, i.e. di-n-butylmagnesium, tert-butylmagnesium chloride, allylmagnesium bromide, m-tolylmagnesium chloride, and methylmagnesium bromide were selected for the potential inductive effect of their hydrocarbon group in leading to various magnesium nanostructures at low te...

The synthesis of 1,4-amino alcohols from THF treated with N-tosyliminobenzyliodinane (PhINTs) followed by a Grignard reagent under mild reaction conditions at room temperature is described herein. Various Grignard reagents were shown to be compatible, furnishing the corresponding 4-substituted-N-1,4-tosylamino alcohols in good to excellent yields. A partial or full detosylation of the N-tosyl-1...

Silylmethyl, tertiary-alkyl, alkenyl, and aryl Grignard reagents underwent intermolecular addition to olefins, such as styrenes, conjugated dienes, and enynes under an air atmosphere to give homologated alcohols. For example, (trimethylsilyl)methylmagnesium chloride and alpha-methylstyrene in ether at room temperature under dry air directly furnished 2-phenyl-4-(trimethylsilyl)-2-butanol in goo...

Commercially available arylboronic acids can easily be converted into chiral boronic esters which subjected to Matteson homologations using Grignard reagents. The best results are obtained in one pot protocols without isolation of the ?-chloroboronic ester intermediates. Alkoxides also used as nucleophiles, but corresponding homologated found not stable.