Abstract
A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Knolker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).
Highlights
Methylation is a fundamental transformation in synthetic chemistry that is widely used for the synthesis and functionalization of fine chemicals.[1]
Following the pioneering work of Grigg on the rutheniumand rhodium-catalyzed methylation of arylacetonitriles and aromatic amines,[8] respectively, there have been a number of subsequent reports describing precious metal-catalyzed Borrowing hydrogen (BH) methylation (Scheme 1A).[9]
Considerable progress has been made in this regard, with well-defined iron, manganese, and cobalt catalysts being employed for a variety of homogeneous BH alkylation processes.[11]
Summary
We gratefully acknowledge the School of Chemistry, Cardiff University for generous support, the EPSRC-funded Bath/ Bristol/Cardiff Catalysis Centre for Doctoral Training (K.P., EP/L016443/1), the EPSRC for a standard research grant (B.D.W.A., EP/R006504/1) and the EPSRC UK National Mass Spectrometry Facility at Swansea University
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