Ingredients
3/4 cup butter, divided 1 package (1/4 ounce) active dry yeast1/2 cup warm water (110° to 115°)1/2 cup warm 2% milk (110° to 115°)2 large eggs, room temperature3 tablespoons bourbon or whiskey4-1/2 to 5 cups all-purpose flour1-1/4 cups sugar, divided 3/4 teaspoon salt2 semisweet baking chocolate bars (4 ounces each) plus 1 ounce, broken into 1/4-ounce pieces (36 pieces total)BOURBON CARAMEL:2/3 cup packed brown sugar1/4 cup butter, cubed1/4 cup bourbon or whiskey1 cup chopped pecansBOURBON CHOCOLATE GLAZE:1 semisweet baking chocolate bar (4 ounces), chopped1/4 cup bourbon or whiskey
Preparation
Microwave 1/4 cup butter until melted. Dissolve yeast in warm water and milk; let stand until foamy, about 10 minutes. In another bowl, combine eggs, bourbon and melted butter; stir in 2 cups flour, 1/4 cup sugar, salt and yeast mixture. Beat on medium speed 3 minutes. Stir in enough remaining flour to form a soft dough.
Turn dough onto a floured surface; knead until smooth and elastic, 6-8 minutes. Place in a greased bowl, turning once to grease the top. Cover; refrigerate overnight.
Punch down dough. Turn onto a lightly floured surface; divide and shape into 36 rolls. Flatten rolls into circles; place 1 chocolate piece in center of each. Fold dough over filling; pinch edges well to seal. Melt remaining butter; pour into a shallow bowl. Place remaining sugar in another shallow bowl. Dip balls in butter, allowing excess to drip off, then roll in sugar.
For bourbon caramel, bring brown sugar, butter and bourbon to a boil in a small saucepan over medium heat. Cook and stir 3 minutes. Pour half of the caramel into a greased 10-in. fluted tube pan; layer with half the pecans and half the dough balls; repeat. Cover with a kitchen towel; let rise in a warm place until doubled, about 45 minutes.
Preheat oven to 350°. Place a sheet of foil on bottom oven rack. Bake on middle oven rack until golden brown, 50-55 minutes. (Cover loosely with foil for last 10-15 minutes if top browns too quickly.) Cool in pan 10 minutes before inverting onto a serving plate. Meanwhile, for bourbon chocolate glaze, melt chocolate in a small heavy saucepan over medium-low heat. Remove from heat; stir in bourbon until smooth. Drizzle glaze over warm bread.