Abstract
Pinacol boronic esters are highly valuable building blocks in organic synthesis. In contrast to the many protocols available on the functionalizing deboronation of alkyl boronic esters, protodeboronation is not well developed. Herein we report catalytic protodeboronation of 1°, 2° and 3° alkyl boronic esters utilizing a radical approach. Paired with a Matteson-CH2-homologation, our protocol allows for formal anti-Markovnikov alkene hydromethylation, a valuable but unknown transformation. The hydromethylation sequence was applied to methoxy protected (-)-Δ8-THC and cholesterol. The protodeboronation was further used in the formal total synthesis of δ-(R)-coniceine and indolizidine 209B.
Highlights
All publication charges for this article have been paid for by the Royal Society of Chemistry
The boron moiety can be converted into a broad range of functional groups.[2,6]
In particular the pinacol boronic esters, which are usually bench stable,[22] easy to purify and o en even commercially available have played a prominent role. These features are attractive for chemical transformations, where the valuable boron moiety remains in the product
Summary
All publication charges for this article have been paid for by the Royal Society of Chemistry. Catalytic protodeboronation of pinacol boronic esters: formal anti-Markovnikov hydromethylation of alkenes† In contrast to the many protocols available on the functionalizing deboronation of alkyl boronic esters, protodeboronation is not well developed.
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