Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion

• Published in: Nature (London) Vol. 451; no. 7177; pp. 417 - 424
• Main Authors: Davies, Huw M. L, Manning, James R
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 24.01.2008; Nature Publishing; Nature Publishing Group
• Subjects: Animals; Biological Products - chemical synthesis; Biological Products - chemistry; Carbenes; Carbon; Carbon - chemistry; Catalysis; Catalysts; Chemical bonds; Chemical reactions; Chemical synthesis; Chemistry; Communities; Exact sciences and technology; Humanities and Social Sciences; Hydrocarbons - chemistry; Hydrogen; Hydrogen - chemistry; Hydrogen bonds; Insertion; multidisciplinary; Natural products; Organic chemistry; Organic compounds; Pharmaceutical Preparations - chemical synthesis; Pharmaceutical Preparations - chemistry; review-article; Science; Science (multidisciplinary); Synthesis; United States; Carbene; Enantioselectivity; Functionalization; Organic free biradical; Insertion; Nitrene; Intermolecular reaction; Review; Natural compound; Potential; Chemical synthesis; Ylidene complex
• ISSN: 0028-0836; 1476-4687
• DOI: 10.1038/nature06485

Novel reactions that can selectively functionalize carbon-hydrogen bonds are of intense interest to the chemical community because they offer new strategic approaches for synthesis. A very promising 'carbon-hydrogen functionalization' method involves the insertion of metal carbenes and nitrenes into C-H bonds. This area has experienced considerable growth in the past decade, particularly in the area of enantioselective intermolecular reactions. Here we discuss several facets of these kinds of C-H functionalization reactions and provide a perspective on how this methodology has affected the synthesis of complex natural products and potential pharmaceutical agents.