Copper-Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β-Borylenones

Angewandte Chemie
Li-Jie Cheng, Neal P Mankad

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 (B2 pin2 ), 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.

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Citations

Jun 6, 2019·Organic & Biomolecular Chemistry·Yuan HuangM Kevin Brown
May 28, 2020·Chemical Society Reviews·Li-Jie Cheng, Neal P Mankad
Nov 6, 2020·Organic & Biomolecular Chemistry·Bing-Xue ShenQing-An Chen
Apr 22, 2021·Accounts of Chemical Research·Li-Jie Cheng, Neal P Mankad
Jun 8, 2021·Chemical Science·Egor M LarinMark Lautens
Dec 19, 2019·Journal of the American Chemical Society·Li-Jie Cheng, Neal P Mankad
Sep 29, 2020·Journal of the American Chemical Society·Minqi ZhouXingang Zhang
Nov 2, 2021·Organic Letters·Pinwen CaiDennis Gillingham
Nov 23, 2021·Organic & Biomolecular Chemistry·Javeed Ur RasoolQazi Naveed Ahmad

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