Cobalt-catalyzed deoxygenative triborylation of allylic ethers to access 1,1,3-triborylalkanes

Wei Jie Teo, Xiaoxu Yang, Yeng Yeng Poon and Shaozhong Ge ()
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Wei Jie Teo: National University of Singapore
Xiaoxu Yang: National University of Singapore
Yeng Yeng Poon: National University of Singapore
Shaozhong Ge: National University of Singapore

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Polyborylated organic compounds have been emerging as versatile building blocks in chemical synthesis. Here we report a selective cobalt-catalyzed deoxygenative 1,1,3-triborylation reaction of allylic ethers with pinacolborane to prepare 1,1,3-triborylalkane compounds. With naturally abundant and/or synthetic cinnamic methyl ethers as starting materials, we have achieved the synthesis of a variety of 1,1,3-triborylalkanes (25 examples). The synthetic utility of these 1,1,3-triborylalkanes is demonstrated through site-selective allylation, protodeborylation, and consecutive carbon-carbon bond-forming reactions. Mechanistic studies including deuterium-labeling and control experiments suggest that this 1,1,3-triborylation reaction proceeds through initial cobalt-catalyzed deoxygenative borylation of allylic ethers to form allylic boronates followed by cobalt-catalyzed 1,1-diborylation of the resulting allylic boronates.

Date: 2020
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DOI: 10.1038/s41467-020-19039-7

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