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Preheat oven to 425°F. Lightly grease a baking sheet. Combine tomatoes, sugar, chili powder, and 1 cup water in a small saucepan. Simmer, stirring occasionally, until completely broken down and glossy, 35 to 40 minutes.
Meanwhile, combine bread and Parmesan in a food processor. Pulse until coarsely crumbled, 12 to 14 times. Spread on prepared baking sheet. Bake until golden brown, 4 to 5 minutes.
Heat oil in a large cast-iron skillet over medium-high heat. Add broccoli, cut sides down, and cook until golden brown, 5 to 6 minutes. Flip and season with salt and pepper. Transfer to oven and bake until just tender, 14 to 16 minutes. Top broccoli with breadcrumbs and serve with tomato jam alongside.