Direct Formation and Reaction of Functionalized thienyl-Based Organocopper Reagents

Complex Biohopanoids Synthesis: Efficient Anchoring of Ribosyl Subunits onto a C30 Hopane

“…In comparison with the methodology implying a "zero-valent" [41] organocopper intermediate, this procedure appeared more convenient and easier to scale up. As demonstrated previously, hopanoid 37 could be transformed into bacteriohopanetetrol (4) and glycoside 1.…”

Steroids as chiral model compounds for selective reactions with metals

“…Reactions with different species of Rieke copper [28][29][30] proved to be more successful. In particular, the reaction of Li 2-thienylcyanocuprate [28] with Scheme 10. Synthesis of the provitamin of (24R)-24,25-dihydroxyprovitamin D 3 .…”

“…Other 22-bromo steroids have been employed as model compounds in lithiation procedures, but the yields after quenching were not very satisfactory [27]. Reactions with different species of Rieke copper [28][29][30] proved to be more successful. In particular, the reaction of Li 2-thienylcyanocuprate [28] with Scheme 10.…”

“…In general, ligands derived from the trans-amino alcohols are more active than those prepared from the cis-amino alcohols. The cis-salicylideneimines (27,28) and the cis-derivatives (35a and 35b) are inactive. Obviously, the nearly planar environment of the copper in complexes obtained with tridentate ligands and the higher stability of the dinuclear structure of the ciscompounds are not ideal for the catalyst.…”

Synthesis and reactivity of succinylthioimidazolium salts: A unified strategy for the preparation of thioethers

“…In this regard, organocupprate which was prepared from Rieke copper and para-92 bromoanisol gave only traces of arylsulfide 157 (Table 9, Entry 1). [268] Also the corresponding zincate obtained by transmetallation of para-methoxyphenylmagnesium bromide with an excess of zinc bromide gave only minor yields of 157 (Table 9, Entry 2).…”