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Formation of seven-membered rings by RCM of vinyl bromides

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 (BrCl) was noted as a side reaction under RCM conditions.
0936-5214
Ajavakom, Vachiraporn
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Pandokrak, Potchanee
83904219-68f5-49b5-a024-fd4cfb86e036
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Moustafa, Gamal
1a452cdc-4856-4243-9864-b391fb115f07
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Hill-Cousins, Joseph T.
3fd2a389-1612-4d9d-8322-afcc0c401ada
Ajavakom, Anawat
5bfbc657-18ac-4cfd-8e6c-3969f2a51e0e
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Ajavakom, Vachiraporn
f993a9cd-e859-41c0-995b-a40f1bf19a7c
Pandokrak, Potchanee
83904219-68f5-49b5-a024-fd4cfb86e036
Salim, Sofia S.
d5de5263-b418-469b-b3f5-bdd05ee48387
Moustafa, Gamal
1a452cdc-4856-4243-9864-b391fb115f07
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Hill-Cousins, Joseph T.
3fd2a389-1612-4d9d-8322-afcc0c401ada
Ajavakom, Anawat
5bfbc657-18ac-4cfd-8e6c-3969f2a51e0e
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).

Record type: Article

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 (BrCl) was noted as a side reaction under RCM conditions.

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a-1845-4195 - Accepted Manuscript
Restricted to Repository staff only until 6 May 2023.
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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
ORCID for Gamal Moustafa: ORCID iD orcid.org/0000-0002-9940-0033
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

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: Gamal Moustafa ORCID iD
Author: Richard K. Bellingham
Author: Joseph T. Hill-Cousins
Author: Anawat Ajavakom

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