Journal article
Synthesis of all‐carbon disubstituted bicyclo[1.1.1]pentanes by iron‐catalyzed Kumada cross‐coupling
- Abstract:
- 1,3‐Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p‐substituted arenes and alkynes. Access to all‐carbon disubstituted BCPs via cross coupling has to date been limited to use of the BCP as the organometallic component, which restricts scope due to the harsh conditions typically required for the synthesis of metallated BCPs. Here we report a general method to access 1,3‐C‐disubstituted BCPs from 1‐iodo‐bicyclo[1.1.1]pentanes (iodo‐BCPs) by direct iron‐catalyzed cross‐coupling with aryl and heteroaryl Grignard reagents. This chemistry represents the first general use of iodo‐BCPs as electrophiles in cross‐coupling, and the first Kumada coupling of tertiary iodides. Benefiting from short reaction times, mild conditions, and broad scope of the coupling partners, it enables the synthesis of a wide range of 1,3‐C‐disubstituted BCPs including various drug analogues.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 1.4MB, Terms of use)
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- Publisher copy:
- 10.1002/anie.202004090
Authors
+ European Commission
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- Funder identifier:
- https://ror.org/00k4n6c32
- Grant:
- 786633
- Programme:
- Marie Skłodowska-Curie Actions
+ Engineering and Physical Sciences Research Council
More from this funder
- Funder identifier:
- https://ror.org/0439y7842
- Grant:
- EP/S013172/1
- EP/L015838/1
- Publisher:
- Wiley
- Journal:
- Angewandte Chemie International Edition More from this journal
- Volume:
- 59
- Issue:
- 29
- Pages:
- 11866-11870
- Publication date:
- 2020-05-14
- Acceptance date:
- 2020-04-28
- DOI:
- EISSN:
-
1521-3773
- ISSN:
-
1433-7851
- Pmid:
-
32346946
- Language:
-
English
- Keywords:
- Pubs id:
-
1103385
- Local pid:
-
pubs:1103385
- Deposit date:
-
2020-05-10
Terms of use
- Copyright holder:
- Nugent et al.
- Copyright date:
- 2020
- Rights statement:
- © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Licence:
- CC Attribution (CC BY)
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