Science of Synthesis

Frost, C. G.; Le Nôtre, J., Science of Synthesis, (2008) 36, 325.

The reaction of arylboronic acids with aldehydes in the presence of a catalytic amount of a palladium(0) complex can provide the corresponding secondary alcohols, although this protocol is currently less developed than the corresponding process with rhodium (Section ‌36.1.7.3.1‌). The addition of an arylboronic acid to an aldehyde was noted as a side reaction in the application of phosphapalladacyclic complexes to catalytic C—C bond-forming reactions.[‌343‌] A more general protocol has been developed that employs palladium(0) complexes in the presence of a base and chloroform; no catalytic activity is observed without chloroform.[‌344‌] The authors noted interesting electronic effects in both the arylboronic acid and aldehyde component. The reaction is facilitated by electron-withdrawing groups on the aldehyde to provide high yields of alcohol ‌113‌, whereas electron-donating groups afford lower yields of product, as shown by the formation of alcohol ‌114‌ (‌Scheme 63‌). An alternative arylation reaction of aromatic aldehydes with arylboronic acids in the absence of chloroform has been described.[‌345‌]

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References

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• 8.Meeeee-Meee, (8888) M 88e, 8888.