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.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Teo WJ,Yang X,Poon YY,Ge Sdoi
10.1038/s41467-020-19039-7subject
Has Abstractpub_date
2020-10-15 00:00:00pages
5193issue
1issn
2041-1723pii
10.1038/s41467-020-19039-7journal_volume
11pub_type
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