Phenylethyl bromide, carbonylation

Racemic a-phenylethyl bromide is carbonylated under phase-transfer conditions with 5 N NaOH and dichloromethane containing bis-(dibenzylideneacetone)Pd(O) and a chiral 2-substituted 3,1,2-oxaza-phospholane to give a-phenylpropionic acid in moderate ee (Scheme 83) (196). The reaction involves kinetic resolution of the bromide with a discriminative slow oxidative addition step. 

Tin Derivatives. 3-(Tri-n-butylstannyl)furan can be converted into a 3-furyl ketone 37 either by a StiUe-type coupling under CO pressure or by acylation with an acid chloride (Scheme 18). When 3-(phenylethyl) -(tii- -butylstannyl)thiophene was allowed to react with benzyl bromide under an atmosphere of CO, formation of the carbonylated product 38 was accompanied by 13% yield of the symmetrical ketone, bis[4-(phenylethyl)thiophen-3-yl] ketone.f In 3,4-bis(tri-n-butylstannyl)furan 39 selective monoacylation can be achieved with acid chlorides. The ketones can subsequently be further carbonylated. ... 

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