Heat oil in large ovenproof skillet over medium-high heat until very hot, about 3 minutes. Add fennel wedges in single layer; sprinkle with 1 teaspoon coarse salt. Cook until fennel begins to brown and soften, turning occasionally, 10 to 12 minutes. Add tomatoes, oregano, garlic, and crushed red pepper; sprinkle with 1 teaspoon coarse salt and 1 teaspoon pepper. Fold together gently.