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Preheat oven to 400˚F and line a sheet pan with parchment paper.
To prepare the chicken, make 3-4 angled slices into each breast, ½-inch apart and being careful not to slice through. Liberally coat each breast with olive oil, Italian seasoning and salt. Nestle 1 tomato slice in each cut. Use smaller tomato slices for the first and last cuts while using larger halves for the center cuts.
Roast in the oven for 40-50 minutes until golden brown, or until internal temperature reaches 165˚F. Sprinkle each breast evenly with parmesan cheese and place under the broiler for 1-2 minutes to melt and crisp the cheese. Remove from oven and transfer to serving platter. Finish with fresh basil and a sprinkling of salt.
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