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Catalyst-free photocyclopropanation of dibromomalonates with alkenes: an approach to multisubstituted cyclopropanes

Catalyst-free photocyclopropanation of dibromomalonates with alkenes: an approach to multisubstituted cyclopropanes
Catalyst-free photocyclopropanation of dibromomalonates with alkenes: an approach to multisubstituted cyclopropanes
We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.
photochemistry, cyclopropanation, catalyst-free, cyclopropane, mechanism
0040-4039
6499-6502
Zhang, Yanbin
1d112312-1a7a-4511-9411-35cab8f6e369
An, Yong
6636e59b-9857-488c-8039-ec8f3f10cce5
Sun, Jing
4db759d9-dc7e-47ce-903b-c507d5b76115
Ding, Aishun
e9d00485-889e-4734-b191-f69d662f53ed
Wang, Yu
6d2a1ba4-6455-40a5-a1f9-514aff2274c9
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Guo, Hao
2e060524-1e5c-47e7-8ee6-b81d25f82d0d
Zhang, Yanbin
1d112312-1a7a-4511-9411-35cab8f6e369
An, Yong
6636e59b-9857-488c-8039-ec8f3f10cce5
Sun, Jing
4db759d9-dc7e-47ce-903b-c507d5b76115
Ding, Aishun
e9d00485-889e-4734-b191-f69d662f53ed
Wang, Yu
6d2a1ba4-6455-40a5-a1f9-514aff2274c9
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Guo, Hao
2e060524-1e5c-47e7-8ee6-b81d25f82d0d

Zhang, Yanbin, An, Yong, Sun, Jing, Ding, Aishun, Wang, Yu, Rios, Ramon and Guo, Hao (2015) Catalyst-free photocyclopropanation of dibromomalonates with alkenes: an approach to multisubstituted cyclopropanes. Tetrahedron Letters, 56 (46), 6499-6502. (doi:10.1016/j.tetlet.2015.10.012).

Record type: Article

Abstract

We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.

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Accepted/In Press date: 4 October 2015
e-pub ahead of print date: 9 October 2015
Published date: 18 November 2015
Keywords: photochemistry, cyclopropanation, catalyst-free, cyclopropane, mechanism
Organisations: Chemistry
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Identifiers

Local EPrints ID: 383675
URI: http://eprints.soton.ac.uk/id/eprint/383675
DOI: doi:10.1016/j.tetlet.2015.10.012
ISSN: 0040-4039
PURE UUID: 1a216f01-bf9f-4645-a4b8-0c19a471f83e
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 09 Nov 2015 16:55
Last modified: 15 Mar 2024 05:22

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Contributors

Author: Yanbin Zhang
Author: Yong An
Author: Jing Sun
Author: Aishun Ding
Author: Yu Wang
Author: Ramon Rios ORCID iD
Author: Hao Guo

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