Grignard carbonyl
Additional step: reactant 2 has to be transformed into Griganrd reagent (RMgX) first.
SMARTS: [#6:1][C:2]#[#7;D1].[Cl,Br,I][#6;$([#6]~[#6]);!$([#6]([Cl,Br,I])[Cl,Br,I]);!$([#6]=O):3]>>[#6:1][C:2](=O)[#6:3]
Conditions
Reactant 1: nitrile.
Reactant 2: arylhalide.
R1, R2: aryl, alkyl. X: Cl, Br, I.
References
Grignard, V. C. R. Acad. Sci. 1900, 130, 1322–1324.
Grignard, V. Ann.Chim. 1901, 7, 433–490.
Other sources
Organic chemistry
Wikipedia