Novel One-Pot Approach to Synthesis of Indanones through Sb(V)-Catalyzed Reaction of Phenylalkynes with Aldehydes

Abstract

Catalytic SbF5 and the use of EtOH as an additive efficiently converted a mixture of phenylalkynes and aldehydes to indanone compounds in one pot, and the reaction stereoselectively afforded the corresponding 2,3-disubstituted indanones as a single trans-isomer.

Novel ynamide structural analogues and their synthetic transformations

“…When using diphenyl ketene 65-e, allenyl amide 66 was also isolated in addition to the expected cyclobutenone 63-e. The formation of 66 is likely a result of pericyclic ring opening of the oxetene intermediate 67, [45][46][47][48][49][50][51][52][53][54] which could be envisioned through a hetero-[2 + 2] pathway (Scheme 13).…”

Regioselective Synthesis of Indanones

“…For example, indanones belonging to the Pterosin sesquiterpene family exhibit antimicrobial, 1 antispasmodic 2 and cytotoxic activity, 3 while the synthetic indanocine shows antiproliferative activity 4 ( Figure 1). The development of chemo-and regioselective synthetic methodology toward indanones is therefore of considerable importance.The main methods for the synthesis of indanones are (intramolecular) Friedel-Crafts acylation, 5 Nazarov cyclization, 6 and various transition-metal-catalyzed ring-closing reactions. 7 Indanones can also be accessed by the one-pot reaction of α,β-unsaturated carboxylic acids with benzene derivatives using polyphosphoric acid (PPA).…”

“…The main methods for the synthesis of indanones are (intramolecular) Friedel-Crafts acylation, 5 Nazarov cyclization, 6 and various transition-metal-catalyzed ring-closing reactions. 7 Indanones can also be accessed by the one-pot reaction of α,β-unsaturated carboxylic acids with benzene derivatives using polyphosphoric acid (PPA).…”

Expanding the frontier of gold-catalyzed cyclizations and rational ligand design.

“…17,27,[75][76][77][78][79][80]142 However, the fact that the oxygen-transfer reaction of 2-alkynyl-1,5-diketones or 2-alkynyl-5-ketoesters could be completed in minutes at room temperature, and with higher yields than previously reported oxygen transfer prompted us to propose an alternative [4+2] mechanism (Scheme 20, bottom). We envisioned that a five-membered ring furanium C 8,20,[143][144][145][146][147][148][149][150][151][152] would be much easier to form than the seven-membered ring oxonium A, this action is followed by a [4+2] upfield chemical shift [153][154][155] was found on carbon 1 in the substrate, whereas no chemical shift change occurred on carbon 2.…”

“…[63][64][65][66][67][68][69][70][71][72][73][74] In this regard, many Lewis or Brønsted acid catalyzed intermolecular or intramolecular alkyne-carbonyl metathesis reactions have been extensively developed (Scheme 17, top). [75][76][77][78][79][80] Notably, by using tethered alkynylketones as the substrates,…”