Chinese Journal of Organic Chemistry >
Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method
Received date: 2020-10-07
Revised date: 2020-12-16
Online published: 2021-02-07
Supported by
Project of Enhancing School with Innovation of Guangdong Ocean University(230419054); College Students Innovation Program of Guangdong Ocean University(580520106); Graduate Education Innovation Program of Guangdong Ocean University(521002082)
1,3-Conjugated olefins are very useful synthetic intermediates. Furthermore, 1,3-diene moiety is an important unit often found in many polymers, natural products and biologically active compounds. For these reasons, the design and synthesis of compounds containing a diene moiety have received considerable attention in organic synthesis and have been extensively studied. Among these methods, the Heck cross-coupling reaction between alkenyl halide and terminal alkene under palladium catalysis has become a powerful tool for the synthesis of dienes. Recently, many research groups have focused on “one-pot method” cascade reactions to form carbon-carbon bond due to not only their convenient and simple operation, but also their high atomic economy. Using terminal alkyne and bis(pinacolato)diboron as starting materials and NaOMe as the base, alkenyl borates were formed, and a series of 1,3-butadienes were directly synthesized via palladium-catalyzed homocoupling reaction of alkenyl borates. The structures of all the compounds were confirmed by 1H NMR and 13C NMR. This one pot method is simple and mild, which provides a simple way for the synthesis of a series of 1,3-butadienes.
Key words: one-pot method; terminal alkyne; alkenyl borate; 1,3-butadiene
Jingru Liang , Bingying Wang , Chengyin Huang , Xiaojun Ye , Yanmei Wen . Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 2116 -2120 . DOI: 10.6023/cjoc202010008
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