Abstract
We have found that in the Baylis–Hillman reactions of N-arylidenediphenylphosphinamides 1 with methyl vinyl ketone (MVK), methyl acrylate or acrylonitrile, the Lewis base and solvent can significantly affect the reaction rate. Using PPh 3 as Lewis base in the reaction of 1 with MVK in DMF, THF or MeCN, the normal Baylis–Hillman adduct 2 was formed in very high yield. In the Baylis–Hillman reaction of 1 with methyl acrylate, the Lewis base Ph 2PMe must be used in order to get a high yield of the Baylis–Hillman adduct 3 . On the other hand, for the reaction of N-arylidenediphenylphosphinamides 1 with acrylonitrile, DABCO is the best Lewis base giving the corresponding Baylis–Hillman adducts 4 in high yields.
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