A palladium catalyst and one of these compounds can be used in a form of coupling that removes a carboxylic acid functionality from an R-COOH and attaches the R to an R' in an R' (R prime)-halide.
Cyclopropanols are synthesized from esters via an in situ formation of one of these compounds in the Kulinkovich reaction. The industrial synthesis of the anti-estrogen receptor positive breast cancer drug Tamoxifen uses a specific kind of these compounds, one type of which can be resolved into precipitates by adding dioxane. A palladium catalyst and one of these compounds can be used in a form of coupling that removes a carboxylic acid functionality from an R-COOH and attaches the R to an R' in an R' (R prime)-halide. Besides Tebbe's and Gilman's reagents, the best-known type of these compounds exists in a Schlenk equilibrium and can be added to carbonyl carbons to yield some form of alcohol. For 10 points, identify these compounds which include Grignard reagents, which contain metals bound to carbon atoms.
Cyclopropanols are synthesized from esters via an in situ formation of one of these compounds in the Kulinkovich reaction.
organometallic compounds [accept organotitaniums during the first two sentences; prompt on "organotitaniums" afterwards; prompt on "organocuprates"; prompt on "organolithiums"; prompt on "organomagnesiums"; prompt on "Gilman's reagent" until mentioned; prompt on "Tebbe's reagent" until mentioned; prompt on "Grignard reagents" until mentioned , because hey, we have to cover all our bases]