Synthesis of All-Carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada Cross-Coupling.
bicyclopentane
bioisosteres
cross-coupling
homogeneous catalysis
iron
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
13 07 2020
13 07 2020
Historique:
received:
19
03
2020
pubmed:
30
4
2020
medline:
30
4
2020
entrez:
30
4
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32346946
doi: 10.1002/anie.202004090
pmc: PMC7383991
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
11866-11870Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
Chemistry. 2015 Apr 7;21(15):5946-53
pubmed: 25703202
Angew Chem Int Ed Engl. 2020 Jul 13;59(29):11866-11870
pubmed: 32346946
Chem Rev. 1996 Dec 19;96(8):3147-3176
pubmed: 11848856
J Med Chem. 2012 Apr 12;55(7):3414-24
pubmed: 22420884
Chemistry. 2014 Apr 14;20(16):4796-805
pubmed: 24596072
Chem Commun (Camb). 2014 May 25;50(40):5187-9
pubmed: 23969613
Chem Res Toxicol. 2016 Apr 18;29(4):564-616
pubmed: 26974882
Angew Chem Int Ed Engl. 2020 Mar 2;59(10):3917-3921
pubmed: 31912941
Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12774-12777
pubmed: 28786520
Angew Chem Int Ed Engl. 2018 Nov 26;57(48):15857-15861
pubmed: 30291667
ACS Med Chem Lett. 2016 Nov 15;8(1):43-48
pubmed: 28105273
Angew Chem Int Ed Engl. 2020 May 18;59(21):8225-8231
pubmed: 32003916
Bioorg Med Chem Lett. 2001 Dec 3;11(23):3049-53
pubmed: 11714608
Angew Chem Int Ed Engl. 2014 Feb 10;53(7):1804-8
pubmed: 24505000
Chemistry. 2020 Apr 1;26(19):4242-4245
pubmed: 31922305
Angew Chem Int Ed Engl. 2019 Sep 16;58(38):13416-13420
pubmed: 31291500
Chemistry. 2011 Oct 17;17(43):11991-3
pubmed: 21922569
Dalton Trans. 2016 Oct 12;45(40):15811-15817
pubmed: 27339002
Acc Chem Res. 2019 Jan 15;52(1):140-150
pubmed: 30592421
Chemistry. 2019 Mar 27;25(18):4590-4647
pubmed: 30387906
Org Lett. 2012 Feb 17;14(4):1066-9
pubmed: 22288653
Org Biomol Chem. 2019 Mar 13;17(11):2839-2849
pubmed: 30672560
Org Lett. 2019 Apr 5;21(7):2408-2411
pubmed: 30869907
Angew Chem Int Ed Engl. 2018 May 4;57(19):5492-5496
pubmed: 29575686
Chem Sci. 2018 Aug 24;9(41):7931-7939
pubmed: 30429998
Chem Commun (Camb). 2008 Jan 7;(1):94-6
pubmed: 18399411
J Med Chem. 2009 Nov 12;52(21):6752-6
pubmed: 19827778
ACS Med Chem Lett. 2017 Apr 24;8(5):516-520
pubmed: 28523103
Nature. 2020 Apr;580(7802):220-226
pubmed: 32066140
Chem Soc Rev. 2012 Feb 7;41(3):979-87
pubmed: 22218700
J Am Chem Soc. 2004 Mar 31;126(12):3686-7
pubmed: 15038701
Chem Commun (Camb). 2005 Sep 7;(33):4161-3
pubmed: 16100589
Chem Commun (Camb). 2006 Apr 7;(13):1398-400
pubmed: 16550279
Chem Sci. 2020 Apr 13;11(19):4895-4903
pubmed: 34122945
Angew Chem Int Ed Engl. 2009;48(31):5586-7
pubmed: 19554587
ChemMedChem. 2017 Apr 20;12(8):590-598
pubmed: 28319646
Angew Chem Int Ed Engl. 2007;46(23):4364-6
pubmed: 17465438
Acc Chem Res. 2015 May 19;48(5):1485-93
pubmed: 25916260
Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11116-11128
pubmed: 29460380
Chem Commun (Camb). 2015 Feb 7;51(11):2111-3
pubmed: 25536275
Chem Sci. 2018 May 21;9(23):5295-5300
pubmed: 29997886
Org Lett. 2014 Dec 5;16(23):6160-3
pubmed: 25401684
J Am Chem Soc. 2009 May 6;131(17):6078-9
pubmed: 19364096
Angew Chem Int Ed Engl. 2020 Jan 27;59(5):1970-1974
pubmed: 31603274