Reduce the wine. Pour 1 cup Merlot into a small saucepan. Simmer until it reduces by half. Set aside to cool.
Mix the dry ingredients. In a large bowl, whisk flour, cocoa, baking soda, baking powder, and salt.
Mix the wet ingredients. In another bowl, whisk eggs, sugar, oil, vanilla, and buttermilk until smooth. Stir in the cooled wine reduction.
Combine. Add the dry ingredients to the wet ingredients. Stir gently until just mixed. Don’t overmix.
Bake. Pour batter into lined cupcake tins, filling each about two-thirds full. Bake at 350°F (175°C) for 18–22 minutes. A toothpick should come out clean. Let cupcakes cool.
Make the frosting. Beat butter until fluffy. Add powdered sugar one cup at a time. Mix in cocoa powder, salt, and 2 tbsp of the wine reduction until smooth.
Frost. Once cupcakes are completely cooled, frost with the Merlot buttercream.