Journal article
Synthesis of 1,3-disubstituted bicyclo[1.1.0]butanes via directed bridgehead functionalization
- Abstract:
- Bicyclo[1.1.0]butanes (BCBs) are increasingly valued as intermediates in ‘strain release’ chemistry for the synthesis of substituted four membered rings and bicyclo[1.1.1]pentanes, with applications including bioconjugation processes. Variation of the BCB bridgehead substituents can be challenging due to the inherent strain of the bicyclic scaffold, often necessitating linear syntheses of specific BCB targets. Here we report the first palladium catalyzed cross-coupling on pre-formed BCBs which enables a ‘late stage’ diversification of the bridgehead position, and the conversion of the resultant products into a range of useful small ring building blocks.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 751.7KB, Terms of use)
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- Publisher copy:
- 10.1039/d1sc01836a
Authors
- Publisher:
- Royal Society of Chemistry
- Journal:
- Chemical Science More from this journal
- Volume:
- 12
- Issue:
- 21
- Pages:
- 7480-7485
- Publication date:
- 2021-04-27
- Acceptance date:
- 2021-04-26
- DOI:
- EISSN:
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2041-6539
- ISSN:
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2041-6520
- Language:
-
English
- Keywords:
- Pubs id:
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1177181
- Local pid:
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pubs:1177181
- Deposit date:
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2021-06-22
- ARK identifier:
Terms of use
- Copyright holder:
- McNamee et al.
- Copyright date:
- 2021
- Rights statement:
- © 2021 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
- Licence:
- CC Attribution (CC BY)
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