The conversion of vinyl triflates into γ'-hydroxy-α,β-enones

The Aminopalladation/Reductive Elimination Domino Reaction in the Construction of Functionalized Indole Rings

“…[23] Use of conditions similar to those reported for the preparation of 2,3-disubstituted indoles [11] (Scheme 11a) and 2-unsubstituted 3-arylin- Scheme 11 doles [19] (Scheme 11b) met with failure, at least with our model system. The N-alkyl derivative 10 Ϫ generated by a competitive base-catalyzed nucleophilic substitution process Ϫ was isolated as the main or the sole reaction product.…”

“…[11] We believed that such a procedure should provide a fundamentally new, straightforward approach to the construction of functionalized pyrrole rings incorporated into indole systems, from arylalkynes containing nitrogen nucleophiles in the ortho position and aryl iodides or vinyl triflates.…”

“…Use of the same conditions as employed in the synthesis of 2,3-disubstituted indoles [11] produced the desired derivatives only in low yields, along with the expected coupling byproducts. With p-iodoacetophenone, for example, the corresponding 3-arylindole 6 and the coupling product 7 were isolated in 23 and 37% yields, respectively (Scheme 7).…”

Chemicals from Alkynes with Palladium Catalysts

“…80 Modified conditions have been the use of a phase-transfer agent in a two-phase system in the case of the hydration of a hydroxylated alkyne 81 or the use of a Nafion/palladium(II) resin in aqueous ethanol for the hydration of 2-methylbut-3-yn-2-ol to 3-hydroxy-3-methylbutan-2-one. 82 …”

Versatile Methodology to Hydrate Alkynes, in the Presence of a Wide Variety of Functional Groups, with Mercury(II) p-Toluensulfonamidate, Under Catalytic, Mild, and Neutral Conditions

“…When using a buffered system like mercury(II) triflate-TMU complex [3] a good functional group compatibility is observed, except for substrates containing acetal or benzyl groups. [4] Other methods have been reported that use catalysts based on gold(I), [5] gold(III), [6] platinum(II), [7] palladium(II), [8] rhodium (III) [9] and ruthenium(II) [10] to form the antiMarkovnikov product. These are very efficient catalyst but the main disadvantage of these methods is the cost of the catalysts based on noble metals.…”