NickelButadiene Catalytic System for the Cross‐Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids

Abstract

The knights who say Ni: A practical and convenient synthetic route to fatty acids involves the Ni‐catalyzed alkylalkyl cross‐coupling of bromoalkanoic acids and alkyl Grignard reagents in the presence of 1,3‐butadiene as an additive (see scheme).

Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

“…To prepare the characteristic long fatty acids, a Ni-catalyzed alkyl-alkyl cross-coupling reaction was also developed, 23 and applied to the total synthesis of EhPIa. To prepare the acylglycerol 7a and 7b (Scheme 1), the long fatty acid derivative 4 was synthesized with a Ni-catalyzed alkyl-alkyl cross-coupling reaction using bromide 2 and Grignard reagent 3 to obtain 4 with a 64% yield.…”

Employing BINOL‐Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica

“…In the final step, these protecting groups were removed by a transition‐metal‐catalyzed deallylation reaction. The compounds 7 a and 7 b were delivered from α‐selective glycosylation using azido‐glucose donor 8 and inositol 9 and subsequent coupling with acylglycerols 10 a and 10 b bearing long‐chain unsaturated lipids, which were prepared by a Ni‐catalyzed alkyl–alkyl cross coupling reaction . The phosphate group of inositol 9 was introduced during an early‐stage in this synthesis through regioselective phosphorylation with BINOL‐derived phosphoryl chlorides having O, S, or Se.…”

Practical large-scale production of dihydrocapsiate, a nonpungent capsaicinoid-like substance

“…The experimental results for the synthesis of MNA (12) are summarized in Table 1. Referring to the method reported by Cahiez et al, 15) the copper-catalyzed alkylation of a Grignard reagent and ethyl ω-haloalkylcarboxylate was examined. As a starting material for obtaining ethyl 8-methylnonanoate, a combination of isoamylbromide and ethyl 5-bromopentanoate (5BPE), or isobutylbromide and ethyl 6-bromohexanoate (6BHE, 9), was considered.…”