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New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis (in special issue on recent advances in organotin chemistry)

New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis (in special issue on recent advances in organotin chemistry)
New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis (in special issue on recent advances in organotin chemistry)
Novel resin-bound organotin reagents have been prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride reagents have been used in a catalytic Stille coupling cycle and the resin-bound distannanes have been used in atom transfer cyclisations and proved to be much more effective than previously described resin-bound distannanes. As expected the use of resin-bound tin reagents facilitated their easy removal at the end of the reaction, and consequently residual tin levels in the organic products were low or negligible. The resin-bound distannanes Could not, however, be successfully used for the palladium catalysed stannylation of a simple aryl iodide, which would have provided a useful approach to radiolabeling of aromatic substrates. The reasons for the failure in the stannylation process is unclear but crystal structure evidence indicates that there is a hypervalent interaction between the resin-bound tin atom and an adjacent ether oxygen which may effect the reactivity of the tin intermediates in the stannylation sequence.
organotin, distannane, solid-phase, stille coupling, atom transfer transfer cyclization reactions, linked polystyrene support, alpha-iodo esters, radical reactions, convenient synthesis, stannyl radicals, stille reaction, tin hydrides, carbon bond, palladium
0022-328X
1466-1475
Hernán, Alejandro G.
edee8766-2228-4dfd-8fb6-10cc27c4efc5
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Hernán, Alejandro G.
edee8766-2228-4dfd-8fb6-10cc27c4efc5
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Hernán, Alejandro G., Horton, Peter N., Hursthouse, Michael B. and Kilburn, Jeremy D. (2006) New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis (in special issue on recent advances in organotin chemistry). Journal of Organometallic Chemistry, 691 (8), 1466-1475. (doi:10.1016/j.jorganchem.2005.11.031).

Record type: Article

Abstract

Novel resin-bound organotin reagents have been prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride reagents have been used in a catalytic Stille coupling cycle and the resin-bound distannanes have been used in atom transfer cyclisations and proved to be much more effective than previously described resin-bound distannanes. As expected the use of resin-bound tin reagents facilitated their easy removal at the end of the reaction, and consequently residual tin levels in the organic products were low or negligible. The resin-bound distannanes Could not, however, be successfully used for the palladium catalysed stannylation of a simple aryl iodide, which would have provided a useful approach to radiolabeling of aromatic substrates. The reasons for the failure in the stannylation process is unclear but crystal structure evidence indicates that there is a hypervalent interaction between the resin-bound tin atom and an adjacent ether oxygen which may effect the reactivity of the tin intermediates in the stannylation sequence.

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More information

Published date: 2006
Keywords: organotin, distannane, solid-phase, stille coupling, atom transfer transfer cyclization reactions, linked polystyrene support, alpha-iodo esters, radical reactions, convenient synthesis, stannyl radicals, stille reaction, tin hydrides, carbon bond, palladium

Identifiers

Local EPrints ID: 44462
URI: http://eprints.soton.ac.uk/id/eprint/44462
ISSN: 0022-328X
PURE UUID: b869816a-935a-4850-b821-5d399b127759
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 02 Mar 2007
Last modified: 26 Nov 2019 01:53

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