Abstract
A novel class of triarylmethanes (TRAMs) containing one or two biaryl moieties was synthesized efficiently through the Pd(PPh 3 ) 4 -catalyzed Suzuki–Miyaura cross-coupling reaction of brominated TRAMs with arylboronic acid derivatives. We also demonstrate that brominated TRAMs can be efficiently functionalized via a one-pot, two-step Pd-catalyzed Heck-type process. This protocol provides convenient access to diverse vinylated TRAMs that are generally not obtained by using the common synthetic methods for TRAMs.
Highlights
Biaryls are privileged templates that are frequently found in natural products, functional materials, polymers, liquid crystals, chiral reagents, and biologically active compounds
Likewise, brominated TRAMs 10a–h were subjected to the Suzuki coupling reaction with arylboronic acid derivatives 11a–d to produce the corresponding coupling products, and the results are shown in Scheme 3
We examined the reactivity of TRAM 10c in the coupling reaction with arylboronic acids
Summary
Biaryls are privileged templates that are frequently found in natural products, functional materials, polymers, liquid crystals, chiral reagents, and biologically active compounds. They are employed as building blocks in organic synthesis and ligands for homogeneous catalysis [1,2]. (Scheme 1C) [11], and the Friedel–Crafts alkylation reaction of veratrole 5 with 3 catalyzed by Bi(OTf) under solvent-free conditions (Scheme 1D) [12] as well as p-TsOH-catalyzed functionalization reactions of substituted hydroquinones 7 with benzhydryl alcohols 8 (Scheme 1E) [13] This limitation on scope originates from three determining factors: (i) Aryland heteroarylboronic acids are commercially available with a greater diversity than biarylaldehyde derivatives. As part of an ongoing program on extending the synthetic applications of TRAMs [12,21,22,23], we describe our efforts toward the functionalization of TRAMs via the Suzuki–Miyaura and Heck-type reactions of brominated TRAMs with arylboronic acids and olefins
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