通过分子间自由基和亲核加成反应实现烯烃和炔烃的双官能化。
Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions.
机构信息
College of Biological Science and Technology, Beijing Forestry University, 35 Qinghua East Road, Beijing 100083, China.
Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA.
出版信息
Molecules. 2020 Dec 28;26(1):105. doi: 10.3390/molecules26010105.
Popular and readily available alkenes and alkynes are good substrates for the preparation of functionalized molecules through radical and/or ionic addition reactions. Difunctionalization is a topic of current interest due to its high efficiency, substrate versatility, and operational simplicity. Presented in this article are radical addition followed by oxidation and nucleophilic addition reactions for difunctionalization of alkenes or alkynes. The difunctionalization could be accomplished through 1,2-addition (vicinal) and 1,n-addition (distal or remote) if H-atom or group-transfer is involved in the reaction process. A wide range of moieties, such as alkyl (R), perfluoroalkyl (R), aryl (Ar), hydroxy (OH), alkoxy (OR), acetatic (OCR), halogenic (X), amino (NR), azido (N), cyano (CN), as well as sulfur- and phosphorous-containing groups can be incorporated through the difunctionalization reactions. Radicals generated from peroxides or single electron transfer (SET) agents, under photoredox or electrochemical reactions are employed for the reactions.
烯烃和炔烃是常用且易得的底物，可通过自由基和/或离子加成反应来制备功能化分子。由于其高效、底物通用性和操作简单，双官能化反应是当前的研究热点。本文介绍了通过自由基加成反应、氧化反应和亲核加成反应对烯烃或炔烃进行双官能化的方法。如果反应过程中涉及氢原子或基团转移，则可以通过 1,2-加成（毗邻）和 1,n-加成（远程或远端）实现双官能化。通过双官能化反应可以引入各种基团，如烷基 (R)、全氟烷基 (R)、芳基 (Ar)、羟基 (OH)、烷氧基 (OR)、乙酰氧基 (OCR)、卤素 (X)、氨基 (NR)、叠氮基 (N)、氰基 (CN) 以及含硫和磷的基团。反应中使用过氧化物或单电子转移 (SET) 试剂产生的自由基，在光氧化还原或电化学反应条件下引发反应。
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