Masuda reaction esters

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). 

Kashimura, S., Mural, Y., Ishifune, M., Masuda, H., Murase, H., Shono, T. Electroorganic chemistry. 148. Cathodic coupling of aliphatic esters. Useful reaction for the synthesis of 1,2-diketone and acyloin. Tetrahedron Lett. 1995, 36, 4805-4808. 

Although the method is well tolerating to the presence of free-amino, hydroxy, acetamido, ketone, and acetate ester groups, in several cases yields were rather low. Moreover, the strong deleterious effect of the ortAo-substituent to the halide was found, e.g. 2-iodotoluene and 2-iodopyridine were recovered quantitatively. Masuda s group has developed a similar method based on Pd(dba)2 / P(2-tolyl)3-catalysts suitable for electron-rich pura-substituted aryl iodides. The most serious side-reaction is the... 

Masuda et al. [36] prepared absorbent resins by reacting starch with partially neutralized acrylic acid and a diacrylate ester crosslinking agent, using Ce + as a free radical initiator but without pre-complexation of the polysaccharide. The gel-like reaction product was dried and pulverized. 

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