Formation of seven-membered rings by RCM of vinyl bromides
Formation of seven-membered rings by RCM of vinyl bromides
Grubbs II catalyst mediated ring-closing metathesis (RCM) of mono-brominated dienes is reported to proceed in moderate to good yields (40–80%) where the linking chain contains five atoms, leading to carbocyclic and heterocyclic 7-membered bromo-olefins. Notably, RCM to form 5-, 6- or 8-membered bromo-olefins was unsuccessful, with the exception of one example where RCM afforded diethyl 3-bromocyclohex-3-ene-1,1-dicarboxylate. In this case a bromomethyl-substituted cyclohexene was obtained as a byproduct. The utility of selected bromo-olefin RCM products was demonstrated through their participation in Suzuki-Miyaura reactions. Vinyl halide exchange (BrCl) was noted as a side reaction under RCM conditions.
Ajavakom, Vachiraporn
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Pandokrak, Potchanee
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Salim, Sofia S.
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Moustafa, Gamal
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Bellingham, Richard K.
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Hill-Cousins, Joseph T.
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Ajavakom, Anawat
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Brown, Richard C.D.
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Ajavakom, Vachiraporn
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Pandokrak, Potchanee
83904219-68f5-49b5-a024-fd4cfb86e036
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Moustafa, Gamal
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Bellingham, Richard K.
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Hill-Cousins, Joseph T.
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Ajavakom, Anawat
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Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Ajavakom, Vachiraporn, Pandokrak, Potchanee, Salim, Sofia S., Moustafa, Gamal, Bellingham, Richard K., Hill-Cousins, Joseph T., Ajavakom, Anawat and Brown, Richard C.D.
(2022)
Formation of seven-membered rings by RCM of vinyl bromides.
Synlett.
(doi:10.1055/a-1845-4195).
Abstract
Grubbs II catalyst mediated ring-closing metathesis (RCM) of mono-brominated dienes is reported to proceed in moderate to good yields (40–80%) where the linking chain contains five atoms, leading to carbocyclic and heterocyclic 7-membered bromo-olefins. Notably, RCM to form 5-, 6- or 8-membered bromo-olefins was unsuccessful, with the exception of one example where RCM afforded diethyl 3-bromocyclohex-3-ene-1,1-dicarboxylate. In this case a bromomethyl-substituted cyclohexene was obtained as a byproduct. The utility of selected bromo-olefin RCM products was demonstrated through their participation in Suzuki-Miyaura reactions. Vinyl halide exchange (BrCl) was noted as a side reaction under RCM conditions.
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a-1845-4195
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Accepted/In Press date: 6 May 2022
e-pub ahead of print date: 6 May 2022
Identifiers
Local EPrints ID: 457323
URI: http://eprints.soton.ac.uk/id/eprint/457323
ISSN: 0936-5214
PURE UUID: c872ee26-8672-4b5f-ba10-1600c8c2e55b
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Date deposited: 01 Jun 2022 16:38
Last modified: 02 Jun 2022 01:57
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Contributors
Author:
Vachiraporn Ajavakom
Author:
Potchanee Pandokrak
Author:
Sofia S. Salim
Author:
Richard K. Bellingham
Author:
Joseph T. Hill-Cousins
Author:
Anawat Ajavakom
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