A reagent whose commercial name contains the word Alpine and this moiety's name is used in a stereoselective reduction of carbonyls to alcohols called the Midland reduction. The reaction of a catechol derivative containing this moiety with an alkyne and subsequent treatment with bromine yields a trans vinyl compound with this moiety. Compounds with this moiety, such as 9-BBN, may be coupled with organohalides under base and palladium catalysis to yield hydrocarbons in a reaction named for Suzuki. Cis-hydration of olefins may be achieved by synthesis of a trialkyl compound centered on this moiety, followed by treatment with sodium hydroxide and hydrogen peroxide. Application of a sodium salt containing this moiety, which is a weaker analog of lithium aluminum hydride, is the simplest method of adding this functiona
A reagent whose commercial name contains the word Alpine and this moiety's name is used in a stereoselective reduction of carbonyls to alcohols called the Midland reduction. The reaction of a catechol derivative containing this moiety with an alkyne and subsequent treatment with bromine yields a trans vinyl compound with this moiety. Compounds with this moiety, such as 9-BBN, may be coupled with organohalides under base and palladium catalysis to yield hydrocarbons in a reaction named for Suzuki. Cis-hydration of olefins may be achieved by synthesis of a trialkyl compound centered on this moiety, followed by treatment with sodium hydroxide and hydrogen peroxide. Application of a sodium salt containing this moiety, which is a weaker analog of lithium aluminum hydride, is the simplest method of adding this functional group to a compound. For 10 points, name this functional group which is electron-deficient and whose dimeric form contains a 3-center 2-electron bond.
A reagent whose commercial name contains the word Alpine and this moiety's name is used in a stereoselective reduction of carbonyls to alcohols called the Midland reduction.
borane [or boron hydride] 