Liebeskind Srogl Research Articles

Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind–Srogl coupling reaction

Synthesis of medium-sized carbocyclic ketones via the intramolecular B-alkyl Liebeskind–Srogl coupling reaction is described. The sequence of hydroboration of ω-alkenyl thiol ester with 9-BBN and the Liebeskind–Srogl reaction results in the formation of medium-sized carbocyclic ketones with good yield.

Synthesis of diverse dihydropyrimidine-related scaffolds by fluorous benzaldehyde-based Biginelli reaction and post-condensation modifications.

Dihydropyrimidinones and dihydropyrimidinethiones generated from the Biginelli reactions of perfluorooctanesulfonyl-attached benzaldehydes are used as common intermediates for post-condensation modifications such as cycloaddition, Liebeskind–Srogl reaction and Suzuki coupling to form biaryl-substituted dihydropyrimidinone, dihydropyrimidine, and thiazolopyrimidine compounds. The high efficiency of the diversity-oriented synthesis is achieved by conducting a multicomponent reaction for improved atom economy, under microwave heating for fast reaction, and with fluorous solid-phase extractions (F-SPE) for ease of purification.

Regioselective synthesis of multisubstituted pyrazoles via cyclocondensation of β-thioalkyl-α,β-unsaturated ketones with hydrazines

Multisubstituted pyrazoles were efficiently synthesized by cyclocondensation of β-thioalkyl-α,β-unsaturated ketones with hydrazines under relatively mild conditions. A one-pot synthetic protocol through tandem Liebeskind–Srogl cross-coupling/cyclocondensation using α-oxo ketene dithioacetals as the starting materials was also realized for the same purpose.

8-Alkenylborondipyrromethene dyes. General synthesis, optical properties, and preliminary study of their reactivity

A new series of 8-alkenylBODIPY dyes were prepared via the Liebeskind–Srogl cross-coupling starting from 8-thiomethyl-substituted BODIPY. Ten derivatives were prepared using alkenylboronic acids in good to excellent yields (79–97%), and one additional example was prepared from an alkenylstannane in 74% yield. The products display Michael acceptor-like reactivity. The alkenyl fragment quenches the fluorescence of the BODIPY core, which is turned back on by reducing the double bond.

The efficient synthesis of 2-arylpyrimidine acyclic nucleoside phosphonates using Liebeskind–Srogl cross-coupling reaction

A series of novel acyclic nucleoside phosphonates with various aryls attached to the C-2 position of the pyrimidine moiety has been prepared using the Liebeskind–Srogl cross-coupling protocol. The reactions of highly functionalised 2-(methylsulfanyl)pyrimidines with various arylboronic acids were studied and optimised.

Regioselective Syntheses of 2,3‐Substituted Pyridines by Orthogonal Cross‐Coupling Strategies

Abstract2‐Aryl/alkylamino‐3‐aryl I and 3‐aryl/alkylamino‐2‐aryl pyridines II, as important potentially bioactive compounds, were synthesized by applying orthogonal cross‐coupling strategies. Combinations of the Suzuki–Miyaura, Liebeskind–Srogl, and Buchwald–Hartwig protocols gave access to the title compounds in a straightforward and operationally simple manner. Full control over the regioselectivity at the 2‐ and 3‐positions was achieved by using 2,3‐dichloropyridine or 3‐iodo‐2‐(methylthio)pyridine as simple, commercially available starting materials. Within this contribution, efficient and high yielding conditions were developed for the Suzuki–Miyaura cross‐coupling reaction of 2‐substituted 3‐chloropyridines, a transformation formerly underrepresented in the literature. For the synthesis of 3‐alkyl/arylamino‐2‐aryl pyridines, the stability of the methylthio group was exploited under Pd‐catalysis in the absence of a copper source. This even enabled the development of an operationally highly facile (semi)‐one‐pot protocol to access the aforementioned compound class that avoided one purification step. A series of products I and II was prepared by using the developed protocols with excellent regioselectivity and good yields.

Liebeskind–Srogl cross coupling mediated synthesis of verbenachalcone

A flexible and scalable total synthesis of verbenachalcone is achieved in eight linear steps from cheap commercially available starting material, 3-(4-hydroxyphenyl)propanoic acid.

Synthesis of 5‐Aroyldihydropyrimidinones via Liebeskind—Srogl Thiol Ester—Boronic Acid Cross‐Couplings.

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