Cleavage organoboron

K. M. Taba, R. Koster, and W. V. Dahlhoff, Organoboron-disaccharides. 2. 2,6-Anhydro-/ -n-fructofuranosc by O-ethylboron-induced cleavage of sucrose, Synthesis, (1983) 1036-1037. 

Ru-catalyzed Suzuki-type cross-coupling reactions of aniline derivatives and organoboronates have been achieved via unreactive aryl C—N bond cleavage (Equation 11.48) [109]. The proposed reaction pathway is a sequence of oxidative addition of an unreactive aryl C—N bond to the late transition metal complex, followed by transmetalation between the Ru-NR2 species and organoboronates, and reductive elimination. 

It is reasonable that the organoboron selenol can be made in analogy to the procedure used for the preparation of 9-HS-9-BBN by employing HjSe gas. However, the procedure presented here circumvents the use of the highly toxic and disagreeable H2Se gas. Instead it makes use of the facile protolytic cleavage of one BSe— bond of /BSeB< by aniline. The loss of... 

Another example of an ARCIS reaction is the efficient Rh(I)-catalyzed decarboxylative coupling of ethyl benzo[/j]quinoline-10-carboxylate with organoboron compounds, which proceeds through C-C and C-B cleavage with the assistance of an N-containing directing group (Scheme 22.35) [50]. 

Substituted boron halides are known to be useful reagents for ether cleavage (52) and selective haloboration reactions (33-34) under mild conditions. Polymeric homologs of these materials, therefore, may have a potential to show unique properties as reactive polymers. Recently, we reported a polyaddition between boron tribromide and terminal diynes as a novel methodology for the preparation of poly(organoboron halide)s (55). We termed this haloboration polymerization. 

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