84735-52-4Relevant academic research and scientific papers
Generation and Reactivities of Organocerium Reagents
Imamoto, Tsuneo,Kusumoto, Tetsuo,Yokoyama, Masataka
, p. 1042 - 1044 (1982)
Organocerium reagents, prepared in situ by the treatment of organolithium compounds with cerium(III) iodide, exhibit characteristic reactivities toward ketones; at -65 deg C, nucleophilic additions give the corresponding tertiary alcohols in excellent yields; while, at 0 deg C to ca. room temperature, reductive coupling and/or reduction of the ketones prevail.
Carbon-Carbon Bond-Forming Reactions Using Cerium Metal or Organocerium(III) Reagents
Imamoto, Tsuneo,Kusumoto, Tetsuo,Tawarayama, Yoshinori,Sugiura, Yasushi,Mita, Takeshi,et al.
, p. 3904 - 3912 (2007/10/02)
Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents have been investigated.Cerium amalgam is an effective reagent for the chemoselective preparation of homoallylic alcohols from allyl halides and carbonyl compounds.These same reagent can also be satisfactorily employed for the Reformatsky-type reaction of α-halo esters with carbonyl compounds.It has been shown that organocerium(III) reagents are conveniently generated by the reaction of organolithiums with cerium(III)iodide or cerium(III)chloride.The reagents are less basic thanorganolithiums or Grignard reagents, and they react cleanly at -78 to -65 deg C with various carbonyl compounds to afford the addition products in high yields, even though the substrates are susceptible to enolization or metal-halogen exchange with simple organolithiums.The same reagents react also with α,β-unsaturated compounds to yield 1,2-addition products in high selectivity.
