Adjust the oven rack to the middle position and preheat the oven to 375°F.
In a medium bowl, whisk together 1½ cups orange juice, ¼ cup corn syrup, 3 tablespoons honey, 1 tablespoon Dijon mustard, 1 tablespoon distilled white vinegar, red pepper flakes, ⅛ teaspoon salt, and ⅛ teaspoon black pepper.
Place the flour in a shallow dish.
Season the chicken on both sides with salt and pepper. Dredge each breast in flour, shaking off the excess.
Heat the oil in a 12-inch ovenproof skillet over medium heat until shimmering.
Place the chicken skin-side down and cook until well browned and most fat is rendered, about 8 to 14 minutes. (If you don’t hear sizzling after 3 minutes, increase heat to medium-high. If browning too quickly, reduce heat slightly.)
Flip the chicken and cook until lightly browned on the other side, about 5 minutes more. Transfer to a plate.
Discard all but 1 teaspoon of fat from the skillet. Add the minced shallot and cook until softened, about 1 to 2 minutes.
Increase heat to high and pour in the orange juice mixture.
Simmer, stirring occasionally, until the glaze reduces to about 1 cup, 6 to 10 minutes.
Remove from heat and tilt the skillet to pool the glaze. Roll each chicken breast in the glaze to coat evenly.
Place the chicken skin-side down in the skillet.
Transfer the skillet to the oven and bake until the thickest part of the chicken reaches 160°F, about 25 to 30 minutes, flipping skin-side up halfway through.
Remove the chicken from the skillet and let rest on a platter for 5 minutes.
Return the skillet to high heat and cook the glaze until thickened, about 1 minute.
Remove from heat and whisk in the remaining 2 tablespoons orange juice.
Spoon 1 teaspoon of glaze over each chicken breast and serve with extra glaze on the side.