By John G. Verkade (auth.), Dr. Jean-Pierre Majoral (eds.)
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Extra resources for New Aspects in Phosphorus Chemistry II
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5) Catalyst 1b is commercially available. (6) Acid- and base-sensitive alcohols can be efficiently silylated by our approach. Similar yields of silylated alcohols can be obtained with or without a solvent. (7) Catalyst 1b is superior to DMAP, DBU and TMG in the reaction of TBDPSCl with alcohols in DMF. TBDMSCl is very effective in the more convenient solvent acetonitrile and under our conditions it is superior to TBDMS triflate for silylating sterically hindered phenols. Minor disadvantages of 1b are that it cannot be used for alcohol protection with TMSCl (because of an interesting side reaction that is under current investigation) or for the silylation of tertiary alcohols with TBDPSCl.
As was already mentioned in Sects. 1, attempts to isolate 1b from salts of 2 resulted in an oligomeric product. However, 2a(OTf ) is as effective as 2b(Cl) for both dehydrohalogenation and debromination, which suggests that intermediate 1a effects dehydrohalogenation of substrates faster than it forms an oligomer of unknown structure. Pro-azaphosphatrane salt 2k(OTf) in CH3CN also effectively allowed dehydrohalogenation, albeit more slowly than 2a(Cl) and 2b(OTf). The advantage of the approach with 2k (in which both the NaH and the procatalyst and catalyst are insoluble) is easy isolation of spectroscopically pure products (ca.