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Oxidation during reductive cyclisations using Bu3SnH by W.Russell Bowman; Harry Heaney; Benjamin M. Jordan is a Chemistry article available to read on EtoBox.

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## Reductive cyclisations using Bu$GtH include an "oxidarion" step g&e removal of an acidic proton from rhe intermediate cyclised raakal. by Bu3SnH acting as a base, isfavowable. A 'pseudo S& mechanism ir proposed. The use of tri-n-butyltin hydride (Bu3SnH) for the reductive cyclisations of a wide range of substrates has been widely reported1 and is a major synthetic method. These reactions involve radical abstraction of groups such as iodine and bromine by Bu3Sn\* radicals to yield an intermediate radical, cyclisation of the radical thus generated onto an unsaturated bond, and reduction of the new intermediate radical by hydrogen abstraction from BugSnH. However, an increasing number of recent publication&to report 'oxidation' during reductive cyclisations with Bu3SnI-I. The authors all identified the problem but did not provide an explanation for the unusual oxidation step. Cyclisation of aryl radicals onto arenes by various methods is well known.3-9 especially with photochemical catalysis. 7 Re-aromatisation in most examples by loss of H2 from the expected cyclisation product would be a strong driving force but this dihydro product has not been detected in any of the examples. M

Who reads Oxidation during reductive cyclisations using Bu3SnH?

Author

W.Russell Bowman; Harry Heaney; Benjamin M. Jordan

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1991

Language

EN

Field

Chemistry (Physical Sciences)