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Metal-catalyzed hydrofunctionalization of alkenes offers the   potential to control the regioselectivity, diastereoselectivity,   and enantioselectivity of the addition process and to form   products from readily accessible starting materials without the   formation of waste. Metal-catalyzed hydrofunctionalizations also   could be more tolerant of auxiliary functionality than acidcatalyzed   additions and could occur without the rearrangements   that are characteristic of acid-catalyzed additions to alkenes.   Hydroamination (the addition of a N−H bond across an   unsaturated C−C bond) remains one of the most studied   transformations in hydrofunctionalization chemistry,1 but hydroetherification   (the addition of an O−H bond across an   unsaturated C−C bond) is much less developed.   The ether products of hydroetherification are more often   formed by substitution reactions than addition reactions.2 The   electrophiles in substitution reactions are typically prepared by a   multistep sequence that includes oxidation or reduction and   functional group interconversion or activation of an alcohol.   Moreover, these substitution reactions generate salt byproducts.   Alternatively, ethers are formed by acid-catalyzed additions of   alcohols to alkenes.3 However, these additions often require   strong acids and high temperatures, form side products from   isomerization of carbocationic intermediates, and occur without   control of the product stereochemistry. Moreover, acid-catalyzed   additions of phenols to alkenes occur with competitive reaction   of the alkene at the O−H bond and at an ortho or para C−H   bond.4 Metal-catalyzed hydroetherification would exploit the   abundance and stability of alkene starting materials and could   overcome many of the limitations of the classical syntheses of   ethers.   However, current hydroetherification reactions are limited in   scope. Most reported metal-catalyzed hydroetherifications of   unsaturated C−C bonds are intramolecular and occur with C−C   multiple bonds that are more reactive than those of unactivated   alkenes.5 Cationic gold complexes catalyze the cyclization of   allenyl alcohols in high yield with excellent ee, but the reactions   do not occur intermolecularly or with monoenes.6 Likewise, Ir,   Pd, Pt, and lanthanide complexes catalyze intramolecular   additions of alcohols to alkenes and alkynes, but intermolecular   additions to alkenes catalyzed by such complexes are unknown.7   Intermolecular hydroetherification of allenes with both carboxylic   acids and phenols to form allylic ethers has been reported to   occur in high yield and ee in the presence of a Rh catalyst, but the   reactions do not occur with monoenes.8 Finally, intermolecular   additions of alcohols to unstrained, isolated alkenes have been   reported to occur in the presence of triflates of coinage metals.9   In these cases, the reactions form side products that are   characteristic of carbocation intermediates.10