Hydromethylation of Unactivated Olefins
Authors:
Open Access
- 19 June 2015
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 137 (25) , 8046-8049
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.Keywords
Funding Information
- China Scholarship Council
- Bureau of Educational and Cultural Affairs
- National Institute of General Medical Sciences (GM-097444)
This publication has 44 references indexed in Scilit:
- Total Synthesis of (±)-Maoecrystal VJournal of the American Chemical Society, 2012
- Control of Selectivity in the Hydromethylation of Olefins via Ligand Modification in Scandocene CatalystsOrganometallics, 2005
- Lactone-Directed Intramolecular Diels−Alder Cyclization: Synthesis of trans-DihydroconfertifolinThe Journal of Organic Chemistry, 2002
- Zirconocene-catalyzed alkylation of aryl alkenes with alkyl tosylates, sulfates and bromidesTetrahedron Letters, 1998
- Enantioselective Total Synthesis of a Natural Norsesquiterpene of the Calamenene Group by a Silane-Terminated Intramolecular Heck ReactionSynlett, 1995
- Iron(III) Complex Catalyzed Nitrosation of Terminal and 1,2-Disubstituted Olefins with Butyl Nitrite and PhenylsilaneChemistry Letters, 1992
- A New Method for Preparation of Alcohols from Olefins with Molecular Oxygen and Phenylsilane by the Use of Bis(acetylacetonato)cobalt(II)Chemistry Letters, 1989
- Bis(trifluoroacetylacetonato)cobalt(II) Catalyzed Oxidation-Reduction Hydration of Olefins Selective Formation of Alcohols from OlefinsChemistry Letters, 1989
- Oxidation-Reduction Hydration of Olefins with Molecular Oxygen and 2-Propanol Catalyzed by Bis(acetylacetonato)cobalt(II)Chemistry Letters, 1989
- Alkyl groups migration from tetra-alkyl-silanes, -germanes, and -stannanes to carbenium ions, effected by Lewis acids: a novel method for synthesising hydrocarbons with a quaternary carbon atomJournal of the Chemical Society, Chemical Communications, 1980