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Vượt ra ngoài hydroxyl hóa trung gian ferryl: 40 năm cơ chế rebound và hoạt hóa C–H
Tóm tắt
Kể từ báo cáo ban đầu của chúng tôi vào năm 1976, cơ chế hồi phục oxy đã trở thành đặc điểm cơ chế đồng thuận của một loạt các phản ứng chức năng hóa C–H enzymatic và các chất xúc tác biomimetic phân tử nhỏ. Đối với cả chuyển hóa sinh học và các mô hình, một sự trừu tượng nguyên tử hydro ban đầu từ chất nền (R–H) bởi các loài sắt-oxo có hóa trị cao (Fen=O) tạo ra một gốc tự do của chất nền và một hydroxit sắt giảm, [Fen−1–OH ·R]. Cặp gốc tự do bị giam cầm này sau đó phát triển trên một bề mặt năng lượng phức tạp thông qua một số con đường phản ứng, chẳng hạn như hồi phục oxy để tạo ra R–OH, hồi phục về một nguyên tử không phải oxy để tạo ra R–X, chuyển điện tử của gốc tự do sơ khởi để tạo thành carbocation, R+, không bão hòa để tạo thành olefin, và thoát ra khỏi lồng gốc tự do. Những dạng khác nhau của quá trình hồi phục này, thường cạnh tranh lẫn nhau, dẫn đến một loạt các phản ứng chức năng hóa C–H được thực hiện bởi các oxyase chứa sắt. Trong bài đánh giá này, chúng tôi đầu tiên thuật lại lịch sử của các cơ chế hồi phục gốc tự do, các đặc điểm chung của chúng và các trung gian chủ chốt liên quan. Chúng tôi sẽ thảo luận chi tiết về các yếu tố ảnh hưởng đến hành vi của cặp gốc tự do bị giam cầm ban đầu và thời gian tồn tại của các gốc tự do chất nền sơ khởi. Nhiều ví dụ tiêu biểu về chuyển hóa C–H enzymatic được chọn để minh họa cách mà hành vi của cặp gốc tự do [Fen−1–OH ·R] xác định kết quả cuối cùng của phản ứng. Cuối cùng, chúng tôi thảo luận về tiềm năng mạnh mẽ của các quá trình “hồi phục gốc tự do” như một khuôn mẫu chung để phát triển các phản ứng chức năng hóa C–H mới với các chất xúc tác tổng hợp và biomimetic. Chúng tôi hình dung rằng hóa học mới sẽ tiếp tục xuất hiện bằng cách kết nối “hồi phục gốc tự do” enzymatic với hóa học hữu cơ tổng hợp.
Từ khóa
#cơ chế hồi phục gốc tự do #hoạt hóa C–H #oxyase chứa sắt #chuyển hóa enzymatic #phản ứng chức năng hóaTài liệu tham khảo
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