The electrosynthesis of highly encumbered biaryls from aryl o-iodobenzyl ethers by a radical to polar crossover sequence†‡
James E.
Pearce, 
a
Jack
Hodgson,
a
Ana A.
Folgueiras-Amador,
a
Johanna A.
Fish,
a
Robert C.
Carroll,
a
Simon J.
Coles,
a
Philip J.
Parsons,
b
Richard C. D.
Brown
*a
and
David C.
Harrowven
*a
a
Jack
Hodgson,
a
Ana A.
Folgueiras-Amador,
a
Johanna A.
Fish,
a
Robert C.
Carroll,
a
Simon J.
Coles,
a
Philip J.
Parsons,
b
Richard C. D.
Brown
*a
and
David C.
Harrowven
*a
Abstract
Highly encumbered 2,2′,6-tri- and 2,2′,6,6′-tetra-substituted biaryls are readily prepared from aryl ortho-iodobenzyl ethers through mediated cathodic reduction under flow. The reaction proceeds via the stepwise transfer of two electrons: the first to induce loss of iodide and a radical cyclisation, and the second to induce a polar fragmentation.
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