Journal of Organic Chemistry p. 2555 - 2559 (1987)
Update date:2022-08-12
Topics:
Aoyama, Yasuhiro
Tanaka, Yasutaka
Fujisawa, Takeshi
Watanabe, Takamichi
Toi, Hiroo
Ogoshi, Hisanobu
(Octaethylporphyrinato)- or (tetraphenylporphyrinato)rhodium(III) chloride catalyzes the anti-Marcovnikov "hydration" of olefin with NaBH4 and O2 in THF. 1,5-Cyclooctadiene gives rise to cyclooctanol and 1,5-cyclooctanediol (in a ratio of approximately 1:2), and acetylenes are converted directly to alcohols under similar conditions.The initial step in the catalytic reaction of olefin is the hydride and borane transfers from BH4- respectively to RhIII porphyrin and olefin to give hydridorhodium (RhH) porphyrin and alkylborane.The RhH species undergoesoxidation with O2 back to RhIII with concomitant oxidation of alkylborane with retention of configuration.This coupled oxidation of alkylborane is in competition with its nonstereospecific autooxidation without assistance of Rh-H.The present system provides a catalytic modification of hydroboration-oxidation of olefin in the presence of oxygen, as illustrated by the one-pot conversion of 1-methylcyclohexene to (E)-2-methylcyclohexanol with 100 percent regioselectivity and up to 97 percent stereoselectivity.
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