Allylations silver® trifluoromethanesulfonate

The cyclohexadiene complex 29 has been further elaborated to afford either the cydo-hexenone 34 or the cyclohexene 36 in moderate yields (Scheme 1) [21]. The addition of HOTf to 29 generates the oxonium species 33, which can be hydrolyzed and treated with cerium(IV) ammonium nitrate (CAN) to release the cyclohexanone 34 in 43 % yield from 29. Alternatively, hydride reduction of 33 followed by treatment with acid eliminates methanol to generate the r 3-allyl complex 35. This species can be trapped by the conjugate base of dimethyl malonate to afford a cyclohexene complex. Oxidative decomplexation of this species using silver trifluoromethanesulfonate liberates the cyclohexene 36 in 57 % overall yield (based on 29). 

The oligomerization and cooligomerization of conjugated dienes are representative reactions that proceed via transition-metal Jt-allyl intermediates. When (CsMesjRuCljt/ -butadiene) in dichloromethane was treated with an acetone solution of an equimolar amount of silver trifluoromethanesulfonate (AgOTf) in the presence of excess butadiene at ambient temperature, after which the mixture was allowed to react with carbon monoxide (1 atm), a cationic 1,5-cyclooctadiene carbonyl complex, [(C5Me5)Ru(CO)( -l,5-C8Hi2)]OTf, was isolated in 95% yield (Eq. 

Glycosidation Allyl chloroformate, 9 Boron trifluoride etherate, 43 Silver(I) tetrafluoroborate, 273 Silver (I) trifluoromethanesulfonate, 274 Thallium zeolites, 296 Tin(II) trifluoromethanesulfonate, 301 Trichloroacetonitrile, 321 Grignard reactions and reactions of... 

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