I believe you are interested in the stability of the R-O-B bond(s) formed, where R denotes alky (or aryl) group. You need to make a difference between thermal stability and hydrolytic stability. The strength of the B-O bond in boronic esters may depend of the R group and probaly exhibits a correlation with the B-O bond length, see

http://bilder.buecher.de/zusatz/13/13081/13081055_lese_1.pdf

I am sure that the bond strength correlates with the thermal stability.

I did not find a good, freely available review on hydrolytic stability, som ereactions of boronic esters may be found in:

http://www.alfa.com/en/docs/boronicacids.pdf

Probably the oreder of hydrolytic stabiliy may be somewhat different from the thermal stability. It also depends on the pH and on the presence of catalysts, such as metal ions.

Thanks Mr Banhegyi.