Diverse synthesis of C2-linked functionalized molecules via molecular glue strategy with acetylene

Bo Yang, Shaodong Lu, Yongdong Wang and Shifa Zhu ()
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Bo Yang: South China University of Technology
Shaodong Lu: Singfar Laboratories
Yongdong Wang: Singfar Laboratories
Shifa Zhu: South China University of Technology

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract As the simplest alkyne and an abundant chemical feedstock, acetylene is an ideal two-carbon building block. However, in contrast to substituted alkynes, catalytic methods to incorporate acetylene into fine chemicals are quite limited. Herein, we developed a photoredox-catalyzed synthetic protocol for diverse C2-linked molecules via a molecular glue strategy using gaseous acetylene under mild conditions. Initiated by addition of an acyl radical to acetylene, two cascade transformations follow. One involves a double addition for the formation of 1,4-diketones and the other where the intermediate vinyl ketone is intercepted by a radical formed from a heterocycle. In addition to making two new C-C bonds, two C-H bonds are also created in two mechanistically distinct ways: one via a C-H abstraction and the other via protonation. This system offers a reliable and safe way to incorporate gaseous acetylene into fine chemicals and expands the utility of acetylene in organic synthesis.

Date: 2022
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DOI: 10.1038/s41467-022-29556-2

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