Radical chain repair: The hydroalkylation of polysubstituted unactivated alkenes.

Abstract:

:The concept of repair is widely used by nature to heal molecules such as proteins, lipids, sugars, and DNA that are damaged by hydrogen atom abstraction resulting from oxidative stress. We show that this strategy, rather undocumented in the field of synthetic organic chemistry, can be used in a radical chain reaction to enable notoriously intractable transformations. By overcoming the radical chain inhibitor properties of substituted alkenes, the radical-mediated hydroalkylation of mono-, di-, tri-, and even tetrasubstituted unactivated olefins could be performed under mild conditions. With a remarkable functional group tolerance, this reaction provides a general coupling method for the derivatization of olefin-containing natural products.

journal_name

Sci Adv

journal_title

Science advances

authors

Povie G,Suravarapu SR,Bircher MP,Mojzes MM,Rieder S,Renaud P

doi

10.1126/sciadv.aat6031

subject

Has Abstract

pub_date

2018-07-20 00:00:00

pages

eaat6031

issue

7

issn

2375-2548

pii

aat6031

journal_volume

4

pub_type

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