Regioselectivity solvomercuration-reduction

Fig. 3.49. Regioselective hydration of an unsymmetric alkene via solvomercuration/ reduction. The regioselectivity of the solvomercuration/reduction seguence is complementary to that of hydrobora-tion/oxidation/hydrolysis.

Besides H20, simple alcohols or acetic acid can also be added to alkenes by solvomercuration/reduction. Figure 3.50 shows MeOH addition as an example. The regioselectivities of this reaction and of the H20 addition in Figure 3.49 are identical. 

Fig. 3.50. Regioselective methanol addition to an asymmetric alkene via solvomercuration/reduction.

Fig. 3.38. Regioselective hydration of an asymmetric olefin via solvomercuration/reduction.

The regioselectivity of the solvomercuration/reduction sequence is complementary to that of hydroboration/ oxidation/hydrolysis. 

Fig. 1.11. Net reaction (a) for the hydration of olefins (R = CH3, R = H) or (b) for the addition of alcohol to olefins (R = CF3, R = alkyl) via the reaction sequence (1) solvomercuration of the olefin (for mechanism, see Figure 3.37 regioselectivity Figure 3.38) (2) reduction of the alkylmercury compound obtained (for mechanism, see Figure 1.12).

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