Suzuki-cross-coupling

In one case, an unpurified sample of pyrrolyl-bisboronic ester 78, synthesized using conditions described by Masuda and coworkers (2000JOC164), was readily engaged in a Suzuki cross-coupling reaction (95JOC7508) with 5-bromoquinoline 77, giving the desilylated product 79 in 29% overall yield (2002JCS(Pl) 1320). 

Scheme 5.2-18 Pd-catalyzed Suzuki cross-coupling reaction in a [BMIM][BF4] ionic liquid.

The Suzuki cross coupling reaction features in a synthesis of 4-arylcoumarins from the 4-halogeno derivatives c96JCS(Pl)2591> and in a route to the thieno[3,4-c]coumarin (8) from which coumarin 3,4-quinodimethane (9) can be thermally generated <96T3117>. 

SUZUKI CROSS-COUPLING OF ARYLCHLORIDES WITH ARYLBORONIC ACIDS... 

FuNn iONAL Group Tolerance of PdildbrO VIMes.HCI Catalyzed Suzuki Cross-Coupling Reactions of Aryl Chlorides with Phenyi.boronic Acid Derivatives... 

Sterically demanding, water-soluble alkylphosphines 6.10 and 6.11 as ligands have been found to have a high activity for the Suzuki coupling of aryl bromides in aqueous solvents (Eq. 6.35).115 Turnover numbers up to 734,000 mmol/mmol Pd have been achieved under such conditions. Glucosamine-based phosphines were found to be efficient ligands for Suzuki cross-coupling reactions in water.116... 

Substrate reactivity was as expected (Arl > ArBr ArCl). In contrast to the Suzuki cross-coupling, however, Cu and Ru clusters were not active in the Heck reactions, and the activity of Cu/Pd clusters was lower than that of pure Pd clusters. Note the higher activity of Pd clusters prepared in situ (row F) compared to pre-prepared clusters (rows B and G). This increased activity tallies with our findings for Suzuki cross-coupling (7). After reaction, palladium black was observed in all the vials in rows B and G, but not in row F. 

Supported ultra small palladium on magnetic nanopartides used as catalysts for Suzuki cross-coupling and Heck reactions. Advanced Synthesis and Catalysis, 349, 1917-1922. 

Scheme 11.12 Suzuki cross coupling to build the core of complanadine A...

Synthesis of unprotected 4-aryl phenylalanine by Suzuki cross-coupling reactions. 

Scheme 6.19 Scaffold decoration of heterocycles using Suzuki cross-coupling chemistry.

Scheme 6.21 One-pot nucleophilic substitutions and Suzuki cross-coupling reactions for the synthesis of nAChR antagonists.

Further examples of microwave-assisted Suzuki cross-couplings involving supported substrates/catalysts or fluorous-phase reaction conditions are described in Chapter 7. 

In the chemistry described in Scheme 6.151, Coats and a group of researchers from Johnson and Johnson utilized successive reductive aminations and Suzuki cross-coupling reactions to prepare a 192-member library of tropanylidene benz-amides [295], This series of tropanylidene opioid agonists proved to be extremely tolerant with regard to structural variation while maintaining excellent opioid activity. 

---