Recent advances in the applications of [1.1.1]propellane in organic synthesis |
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| Institution: | 1. School of Pharmaceutical and Materials Engineering &Institute for Advanced Studies, Taizhou University, Taizhou 318000, China;2. College of Chemistry, Xiangtan University, Xiangtan 411105, China;3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran;2. School of Chemistry, College of Science, University of Tehran, Tehran, Iran;1. Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan;2. International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan;3. School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan;4. Department of Neuropsychopharmacology, National Institute of Mental Health, National Center of Neurology and Psychiatry, Tokyo 187-8553, Japan;1. Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;2. Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China;3. CCNU-uOttawa Joint Research Centre, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China;1. Department of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Republic of Korea;2. Department of Chemistry, Inha University, Incheon 402-751, Republic of Korea;3. Agency for Defense Development, Daejeon 305-156, Republic of Korea;1. School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China;2. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;3. University of Chinese Academy of Science, Beijing 100049, China |
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| Abstract: | As a highly strained small molecule, 1.1.1]propellane has been widely used in various synthetic transformations owing to the exceptional reactivity of the central bond between the two bridgehead carbons. Utilizing strain-release approaches, the rapid development of strategies for the construction of bicyclo1.1.1]pentane (BCP) and cyclobutane derivatives using 1.1.1]propellane as the starting material has been witnessed in the past few years. In this review, we highlight the most recent advances in this field. Accordingly, the reactivity of 1.1.1]propellane can be divided into three pathways, including radical, anionic and transition metal-catalyzed pathways under appropriate conditions. |
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| Keywords: | [1 1 1]propellane Bicyclo[1 1 1]pentane Cyclobutane Radical Transition metal catalysis Photocatalyst |
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