Bi(OTf)3-catalyzed allylation of epoxides: a facile synthesis of homoallylic alcohols

Bismuth(III) Triflate in Organic Synthesis

“…Therefore, Bi(OTf) 3 was tested as a catalyst for the allylation of various aryl-substituted epoxides (Scheme 15). [33] In all cases, the reaction proceeded rapidly at room temperature with high selectivity. Arylaziridines also underwent cleavage in a regioselective manner.…”

Three‐Membered Heterocycles. Structure and Reactivity

“…Terminal epoxides react with tetraallyltin in the presence of bismuth(III) triflate to give homoallylic alcohols 568. The reaction involves an initial 1,2-shift to form aldehyde 567, which is then attacked by the allyl tin species [624]. A similar but operationally more straightforward protocol is available by combining allyl bromide with indium metal, followed by the addition of epoxide [625].…”

Towards Benign Synthesis of Indenes from Indanones: Zinc‐Mediated Allylation of Ketones in Aqueous Media as a Source of Substituted Indenyl Ligand Precursors

“…The ratio between 3-allyl-7-chloro-4-methyl-1H-indene (32), 4-chloro-7-methyl-1-prop-2-en-(E)-ylidene-indane (33), and 3-allyl-4-chloro-7-methyl-1H-indene (34) was 47 % of 32, 42% of 33and 11 % of 34. 13 21.54 (CH 3 attached to the aromatic ring in 33), 19.40 (CH 3 attached to the aromatic ring in 32), 18.05 (CH 3 attached to the aromatic ring in 34) ppm. EIMS (70 eV): calcd.…”

“…Likewise, Bi(OTf) 3 -catalyzed allylation of indene oxide with tetraallylstannane [18] and the indium(i) chloride mediated allylation of indene oxide with allyl bromide catalyzed by Pd [19] has provided 2-allylhydroxyindane in 85 and 83 % yields, respectively. These allylindanols in turn could be easily envisioned to function as precursors to substituted indenes after elimination of water.…”