Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

Abstract

This account provides an overview of recent work, including our own contribution dealing with Suzuki–Miyaura cross coupling in combination with metathesis (or vice-versa). Several cyclophanes, polycycles, macrocycles, spirocycles, stilbenes, biaryls, and heterocycles have been synthesized by employing a combination of Suzuki cross-coupling and metathesis. Various popular reactions such as Diels–Alder reaction, Claisen rearrangement, cross-metathesis, and cross-enyne metathesis are used. The synergistic combination of these powerful reactions is found to be useful for the construction of complex targets and fulfill synthetic brevity.

Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions

“…Moreover, this kind of TRAM could not be synthesized by Friedel-Crafts alkylation reactions of aldehydes. Double Suzuki-Miyaura coupling reactions using palladium catalysts have been repeatedly reported in organic synthesis [31][32][33][34][35]. Surprisingly, one-pot, double Suzuki coupling reactions of TRAM 10g with two-fold amounts of 11a and 11c under optimal reaction conditions resulted in products 6k and 6l in 78% and 54% yields, respectively.…”

Development of New Synthetic Strategies, Tactics and their Applications

“…Transition metal-catalyzed reactions such as SM crosscoupling [129] is useful for the synthesis of AAA derivatives that provide new option for modification at peptide level [130] and instrumental in developing new strategies for the synthesis of peptide-based drugs. [131] In 2001, Kotha and Lahiri [132] reported for the first time peptide modification by employing a SM cross-coupling.…”

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

“…Thus, numerous multistep total syntheses of organic compounds, including bioactive molecules [31][32][33][34][35] and natural products [36,37], have been performed in a highly chemo-and stereoselective manner through metathesis routes [38][39][40][41][42][43]. In ingeniously elaborated procedures, olefin metathesis has been frequently employed as such or associated with name reactions like Grignard, Wittig, Diels-Alder, Suzuki-Miyaura, Heck, etc., resulting in the assembly of diverse intricate building blocks of the targeted structures [44]. Among the various embodiments of olefin metathesis, the highly chemoselective enyne metathesis reaction [45][46][47][48][49] has led to some of the most striking advances in the development of modern, efficient synthetic protocols [50,51].…”