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. 2015 Jul 1;137(25):8046-9.
doi: 10.1021/jacs.5b05144. Epub 2015 Jun 19.

Hydromethylation of Unactivated Olefins

Hai T Dao  1 , Chao Li  1 , Quentin Michaudel  1 , Brad D Maxwell  2 , Phil S Baran  1
Affiliations

Hydromethylation of Unactivated Olefins

Hai T Dao et al. J Am Chem Soc. .

Abstract

A solution to the classic unsolved problem of olefin hydromethylation is presented. This highly chemoselective method can tolerate labile and reactive chemical functionalities and uses a simple set of reagents. An array of olefins, including mono-, di-, and trisubstituted olefins, are all smoothly hydromethylated. This mild protocol can be used to simplify the synthesis of a specific target or to directly "edit" complex natural products and other advanced materials. The method is also amenable to the simple installation of radioactive and stable labeled methyl groups.

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Figures

Figure 1
Figure 1
(A) Direct olefin hydromethylation, an unsolved problem in organic synthesis. (B) Precedents for hydromethylation. (C) Reaction blueprint with potential complications.
Figure 2
Figure 2
Diversification of complex molecules.
Figure 3
Figure 3
Direct hydromethylation as a step-economic method.
Figure 4
Figure 4
Application in synthesis of stable and radioactive labeled compounds.
See this image and copyright information in PMC

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