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- Title
Copper‐Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β‐Borylenones.
- Authors
Cheng, Li‐Jie; Mankad, Neal P.
- Abstract
Abstract: Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2pin2), and CO. A broad scope of highly functionalized β‐borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all‐carbon tetrasubstituted enones was realized by employing the β‐borylated enone unit, without purification, in a Suzuki–Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products.
- Subjects
NUCLEAR magnetic resonance spectroscopy; CHEMICAL reactions; NUCLEAR magnetic resonance; DICHLOROMETHANE; ALKYNES
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 32, p10485
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201804883