Decarboxylative Borylation and Cross-Coupling of (Hetero)aryl Acids Enabled by Copper Charge Transfer Catalysis.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
13 04 2022
13 04 2022
Historique:
pubmed:
5
4
2022
medline:
15
4
2022
entrez:
4
4
2022
Statut:
ppublish
Résumé
We report a copper-catalyzed strategy for arylboronic ester synthesis that exploits photoinduced ligand-to-metal charge transfer (LMCT) to convert (hetero)aryl acids into aryl radicals amenable to ambient-temperature borylation. This near-UV process occurs under mild conditions, requires no prefunctionalization of the native acid, and operates broadly across diverse aryl, heteroaryl, and pharmaceutical substrates. We also report a one-pot procedure for decarboxylative cross-coupling that merges catalytic LMCT borylation and palladium-catalyzed Suzuki-Miyaura arylation, vinylation, or alkylation with organobromides to access a range of value-added products. The utility of these protocols is highlighted through the development of a heteroselective double-decarboxylative C(sp
Identifiants
pubmed: 35377627
doi: 10.1021/jacs.2c01630
pmc: PMC9676084
mid: NIHMS1850489
doi:
Substances chimiques
Pharmaceutical Preparations
0
Palladium
5TWQ1V240M
Copper
789U1901C5
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
6163-6172Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM134897
Pays : United States
Références
Organometallics. 2019 Jan 14;38(1):3-35
pubmed: 31741548
Angew Chem Int Ed Engl. 2021 Sep 20;60(39):21100-21115
pubmed: 33599363
J Am Chem Soc. 2010 Oct 13;132(40):14006-8
pubmed: 20831188
Angew Chem Int Ed Engl. 2021 Nov 8;60(46):24510-24518
pubmed: 34235828
J Org Chem. 2012 Oct 5;77(19):8678-88
pubmed: 22994557
Molecules. 2020 Jul 31;25(15):
pubmed: 32751973
Chem Soc Rev. 2014 Jan 7;43(1):412-43
pubmed: 24091429
Chem Commun (Camb). 2009 Dec 14;(46):7173-5
pubmed: 19921020
J Org Chem. 2021 Dec 3;86(23):17445-17452
pubmed: 34747599
Chem Rev. 2003 Aug;103(8):2829-44
pubmed: 12914482
Angew Chem Int Ed Engl. 2012 May 21;51(21):5062-85
pubmed: 22573393
Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13197-202
pubmed: 18768813
Science. 2014 Jul 25;345(6195):437-40
pubmed: 24903563
Chemistry. 2000 Apr 3;6(7):1147-52
pubmed: 10785799
Nat Commun. 2015 Jun 29;6:7508
pubmed: 26118733
J Am Chem Soc. 2021 Feb 24;143(7):2729-2735
pubmed: 33576606
J Am Chem Soc. 2009 May 27;131(20):6961-3
pubmed: 19405470
Chem Rev. 2010 Feb 10;110(2):890-931
pubmed: 20028025
Science. 2018 Aug 17;361(6403):668-672
pubmed: 30049785
Org Lett. 2017 Aug 18;19(16):4291-4294
pubmed: 28753311
Chem Rev. 2021 Jan 13;121(1):412-484
pubmed: 33200917
J Am Chem Soc. 2021 Aug 25;143(33):12985-12991
pubmed: 34374534
J Am Chem Soc. 2018 May 23;140(20):6221-6225
pubmed: 29741375
Chem Rev. 2019 Dec 26;119(24):12491-12523
pubmed: 31756093
Chem Rev. 2020 Aug 12;120(15):7348-7398
pubmed: 32597639
Chem Commun (Camb). 2011 May 21;47(19):5455-7
pubmed: 21461411
J Am Chem Soc. 2017 Jun 7;139(22):7440-7443
pubmed: 28514176
ACS Cent Sci. 2017 Jun 28;3(6):647-653
pubmed: 28691077
J Am Chem Soc. 2002 Sep 25;124(38):11250-1
pubmed: 12236722
Tetrahedron. 2019 Feb 1;75(5):584-602
pubmed: 31564756
Angew Chem Int Ed Engl. 2021 Nov 2;60(45):24012-24017
pubmed: 34464007
J Org Chem. 2020 Apr 17;85(8):5362-5369
pubmed: 32174115
Org Biomol Chem. 2006 Jun 21;4(12):2337-47
pubmed: 16763676
Angew Chem Int Ed Engl. 2016 Dec 5;55(49):15319-15322
pubmed: 27862775
Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10514-10520
pubmed: 31162874
Chem Sci. 2019 Sep 3;10(37):8503-8518
pubmed: 32015798
Chemistry. 2015 May 4;21(19):7082-98
pubmed: 25877472
Org Lett. 2010 Mar 5;12(5):1000-3
pubmed: 20187653
Nature. 2018 Nov;563(7729):100-104
pubmed: 30356210
iScience. 2020 Jul 24;23(7):101266
pubmed: 32593954
Acc Chem Res. 2008 Nov 18;41(11):1461-73
pubmed: 18620434
Chem Rev. 2003 Aug;103(8):2763-94
pubmed: 12914480
Chem Rev. 2021 Apr 14;121(7):3561-3597
pubmed: 33596057
J Am Chem Soc. 2021 Apr 14;143(14):5349-5354
pubmed: 33818084
Angew Chem Int Ed Engl. 2012 Jun 11;51(24):5945-9
pubmed: 22492664
Chem Soc Rev. 2011 Oct;40(10):5030-48
pubmed: 21792454
Org Lett. 2007 Jun 21;9(13):2441-4
pubmed: 17542594
ACS Catal. 2021 Jun 18;11(12):7442-7449
pubmed: 35669035
Org Lett. 2007 Apr 26;9(9):1781-3
pubmed: 17411063
Angew Chem Int Ed Engl. 2018 Dec 17;57(51):16721-16726
pubmed: 30358030
iScience. 2019 Sep 27;19:749-759
pubmed: 31491721
Chem Commun (Camb). 2019 May 30;55(45):6445-6448
pubmed: 31099348
J Am Chem Soc. 2016 Oct 5;138(39):12719-12722
pubmed: 27653738
J Am Chem Soc. 2014 Apr 9;136(14):5257-60
pubmed: 24712922
J Am Chem Soc. 2019 Oct 30;141(43):17322-17330
pubmed: 31617708
Chemistry. 2016 Nov 14;22(47):16787-16790
pubmed: 27717095
Chemistry. 2009;15(15):3674-7
pubmed: 19248058
Chem Rev. 2022 Jan 26;122(2):2429-2486
pubmed: 34613698
Org Lett. 2010 Mar 5;12(5):992-5
pubmed: 20121254
Chem Rev. 2013 Jul 10;113(7):5322-63
pubmed: 23509883
Chemistry. 2010 Jun 18;16(23):6861-5
pubmed: 20449854
Angew Chem Int Ed Engl. 2009;48(29):5350-4
pubmed: 19533703
Org Lett. 2019 Jun 7;21(11):4259-4265
pubmed: 31090423
Org Lett. 2009 Dec 17;11(24):5710-3
pubmed: 19924891
J Am Chem Soc. 2006 Sep 6;128(35):11350-1
pubmed: 16939247
Chem Soc Rev. 2018 Oct 1;47(19):7477-7494
pubmed: 30206614
Science. 2006 Aug 4;313(5787):662-4
pubmed: 16888137
Chem Rev. 2022 Jan 26;122(2):1485-1542
pubmed: 34793128
Chemistry. 2014 Feb 3;20(6):1630-7
pubmed: 24435980
Chemistry. 2017 Jun 1;23(31):7382-7401
pubmed: 27859719
J Med Chem. 2016 May 26;59(10):4443-58
pubmed: 26571338
Angew Chem Int Ed Engl. 2015 Dec 21;54(52):15632-41
pubmed: 26509837
Acc Chem Res. 2014 Oct 21;47(10):3174-83
pubmed: 25262745
Chem Commun (Camb). 2011 Jan 14;47(2):677-9
pubmed: 21103597
Angew Chem Int Ed Engl. 2020 Dec 1;59(49):21875-21879
pubmed: 32840957
Org Lett. 2010 Nov 5;12(21):4745-7
pubmed: 20866102
Nat Chem. 2022 Jan;14(1):94-99
pubmed: 34987174