Efficient One-Pot Synthesis of 2-Carbonyl- 1-indanols by Palladium-Catalyzed Tandem Heck–Aldol Reaction

Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry

“…Recently Tu and co-workers 759 have developed an interesting synthesis of 2-carbonylalkyl-1-indanols via the intermolecular Heck reaction between 2-haloarylaldehydes and Baylis-Hillman alcohols followed by intramolecular aldol reaction in a one-pot operation (eq 105). Lee and co-workers 764 have developed an interesting synthesis of 2-(9H-fluoren-9-yl)acrylic acid derivatives via intramolecular Friedel-Crafts reaction of Baylis-Hillman adducts obtained from 2-phenylbenzaldehyde derivatives and propiolic acid esters or amides (and methyl acrylate), following the reaction sequence shown in Scheme 301.…”

Recent Advances in the Synthesis of Indanes and Indenes

“…Synthesis of functionalized indanols 90 by Pd-catalyzedH eck reactiono f2-halobenzaldehydes 88 and Morita-Baylis-Hillman adducts 89 followedb yi ntramolecular aldol-typereaction. [45] Chem. Eur.J.2016, 22,5056 -5094 www.chemeurj.org Ar eaction sequence consistingo ft he Heck reactionb etween aryl diazonium tetrafluoroborates 94 with methyl vinyl ketone followed by hydrogenation,b ase-promotedc arbocyclization and alkylation allowed ac onvenient synthesis of indanones 95 startingf rom simple building blocks (Scheme 37).…”

“…For example,f unctionalized1 -indanols 90 were obtainedb yt he Heck reaction between 2-halobenzaldehydes 88 and Morita-Baylis-Hillman adducts 89,f ollowed by intramolecular aldoltype reaction(Scheme 35). [45] In as imilarw ay,avarietyo f1 -indanone-3-ols 93 were synthesized by the Heck reaction between 2-halobenzaldehydes or 2-haloaryl ketones 91 and butyl vinyl ether 92 followed by ethylene glycol-promoted aldol-type annulation and final hydrolysis, as shown in Scheme 36. [46] Scheme30.…”

Heck Arylations of Baylis-Hillman Adducts

“…The catalysis with Pd(OAc) 2 associated to over-stoichiometric amounts of tetrabutylammonium bromide and sodium hydrogen carbonate can, nevertheless, be efficient, at least in N,N-dimethylformamide, since Tu and coworkers performed efficient domino reactions 37 leading to substituted indanols (Table 5). 38 These synthesis occur via the arylation with an o-halogenated aryl aldehyde of the C=C bond of a Baylis-Hillman adduct, followed by intramolecular aldolization mediated by the basic conditions (Scheme 3). These one-pot Heck-aldol reactions are more efficient with an iodo than a bromo reagent (cf.…”