<p>The monoalkylation of N-methoxypyridinium salts with alkyl
radicals generated from alkenes (via hydroboration with
catecholborane), alkyl iodides (via iodine atom transfer) and
xanthates is reported. The reaction proceeds under neutral conditions
since no acid is needed to activate the heterocycle and does not
require the use of an external oxidant. A rate constant for the addition
of a primary radical to N-methoxylepidinium >107 M–1 s–1 was
experimentally determined. This rate constant is more than one order
of magnitude larger than the one measured for the addition of primary
alkyl radical to protonated lepidine demonstrating the remarkable
reactivity of methoxypyridinium salts towards radicals. The reaction
could be extended to a three component carbopyridinylation of
electron rich alkenes including enol esters, enol ethers and enamides.</p>
<p>The monoalkylation of N-methoxypyridinium salts with alkyl
radicals generated from alkenes (via hydroboration with
catecholborane), alkyl iodides (via iodine atom transfer) and
xanthates is reported. The reaction proceeds under neutral conditions
since no acid is needed to activate the heterocycle and does not
require the use of an external oxidant. A rate constant for the addition
of a primary radical to N-methoxylepidinium >107 M–1 s–1 was
experimentally determined. This rate constant is more than one order
of magnitude larger than the one measured for the addition of primary
alkyl radical to protonated lepidine demonstrating the remarkable
reactivity of methoxypyridinium salts towards radicals. The reaction
could be extended to a three component carbopyridinylation of
electron rich alkenes including enol esters, enol ethers and enamides.</p>
<p>The monoalkylation of N-methoxypyridinium salts with alkyl
radicals generated from alkenes (via hydroboration with
catecholborane), alkyl iodides (via iodine atom transfer) and
xanthates is reported. The reaction proceeds under neutral conditions
since no acid is needed to activate the heterocycle and does not
require the use of an external oxidant. A rate constant for the addition
of a primary radical to N-methoxylepidinium >107 M–1 s–1 was
experimentally determined. This rate constant is more than one order
of magnitude larger than the one measured for the addition of primary
alkyl radical to protonated lepidine demonstrating the remarkable
reactivity of methoxypyridinium salts towards radicals. The reaction
could be extended to a three component carbopyridinylation of
electron rich alkenes including enol esters, enol ethers and enamides.</p>
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