Abstract
This perspective article takes an alternative look at alkali-metal-mediated chemistry (exchange of a relatively inert C-H bond for a more reactive C-metal bond by a multicomponent reagent usually containing an alkali metal and a less electropositive metal such as magnesium or zinc). It pictures that the cleavage of selected C-H bonds can be accompanied by the capturing of the generated anion by the multi (Lewis acid)-(Lewis base) character of the residue of the bimetallic base. In this way small atoms or molecules (hydrides, oxygen-based anions) as well as sensitive organic anions (of substituted aromatic compounds, ethers or alkenes) can be captured. Cleave and capture reactions which occur in special positions on the organic substrate are also included.
Highlights
Avant Garde metallation: mixing the palettes of Grignard and Schlenk s-Block organometallic chemistry has attracted over one hundred years of continuous study since the pioneering works of the European masters, Grignard in organomagnesium chemistry (in recognition of his development of the halides “RMgX”, which are popularly referred to as GrignardRobert Emmet Mulvey was born in Glasgow, Scotland in 1959.He received his first degree (BSc, 1st class Honours) and his Ph.D.(in organolithium chemistry under the direction of Dr RonSnaith) at the University of Strathclyde in 1981 and 1984 respectively
Reagents)[1] and Schlenk in organolithium chemistry[2]. The latter compounds have always been superior in metallation chemistry due to their higher reactivity, which transforms relatively inert, relatively non-polar carbon–hydrogen bonds into more reactive, more polar carbon–metal bonds that in turn can be used in subsequent carbon–carbon or carbon–heteroatom bond formation
For about 50 years, the art of metallation has been dominated by alkyl lithium compounds[3] and sterically inflated lithium amides[4]
Summary
An alternative picture of alkali-metal-mediated metallation: cleave and capture chemistry This perspective article takes an alternative look at alkali-metal-mediated chemistry (exchange of a relatively inert C–H bond for a more reactive C–metal bond by a multicomponent reagent usually containing an alkali metal and a less electropositive metal such as magnesium or zinc). It pictures that the cleavage of selected C–H bonds can be accompanied by the capturing of the generated anion by the multi (Lewis acid)–(Lewis base) character of the residue of the bimetallic base. Cleave and capture reactions which occur in special positions on the organic substrate are included
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