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

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 Commun

journal_title

Nature communications

authors

Teo WJ,Yang X,Poon YY,Ge S

doi

10.1038/s41467-020-19039-7

subject

Has Abstract

pub_date

2020-10-15 00:00:00

pages

5193

issue

1

issn

2041-1723

pii

10.1038/s41467-020-19039-7

journal_volume

11

pub_type

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