Recent advances in palladium-catalyzed (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides.
Journal
Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838
Informations de publication
Date de publication:
03 Aug 2021
03 Aug 2021
Historique:
pubmed:
20
7
2021
medline:
20
7
2021
entrez:
19
7
2021
Statut:
ppublish
Résumé
Palladium has proven to be effective in catalyzing the (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides. Through the employment of appropriate ambiphilic coupling partners, efficient annulation of a variety of allenes, 1,3-dienes, strained alkenes, styrenes, and other C[double bond, length as m-dash]C bond variants can be achieved to provide direct access to numerous useful hetero- and carbocyclic scaffolds. In this Feature Article, we summarize palladium-catalyzed (hetero)annulation methods reported since 2005 (spanning just over 15 years) and discuss outstanding challenges in this area of study.
Identifiants
pubmed: 34278397
doi: 10.1039/d1cc02836g
pmc: PMC8364377
mid: NIHMS1723171
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
7610-7624Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM125052
Pays : United States
Références
Chem Commun (Camb). 2018 Jan 31;54(10):1213-1216
pubmed: 29336446
Angew Chem Int Ed Engl. 2004 May 3;43(19):2514-8
pubmed: 15127439
Org Biomol Chem. 2014 May 21;12(19):3045-61
pubmed: 24691752
Angew Chem Int Ed Engl. 2017 Jun 1;56(23):6641-6645
pubmed: 28467624
Org Lett. 2019 Apr 5;21(7):2048-2051
pubmed: 30901225
Org Biomol Chem. 2020 Mar 18;18(11):2148-2162
pubmed: 32134098
J Org Chem. 2018 Mar 2;83(5):2592-2600
pubmed: 29419292
Org Biomol Chem. 2019 Mar 6;17(10):2651-2656
pubmed: 30778484
Chem Commun (Camb). 2015 Feb 14;51(13):2613-6
pubmed: 25571940
Chem Commun (Camb). 2018 Aug 23;54(69):9595-9598
pubmed: 30094419
Chemistry. 2020 Nov 17;26(64):14565-14569
pubmed: 32584444
J Org Chem. 2006 Nov 24;71(24):9128-38
pubmed: 17109538
J Org Chem. 2009 Feb 20;74(4):1673-8
pubmed: 19143500
J Am Chem Soc. 2015 Aug 5;137(30):9579-82
pubmed: 26190818
J Am Chem Soc. 2009 Apr 15;131(14):5042-3
pubmed: 19296680
J Org Chem. 2009 Jun 5;74(11):4426-8
pubmed: 19405503
Org Lett. 2020 May 1;22(9):3591-3595
pubmed: 32306739
Org Lett. 2007 Apr 26;9(9):1761-4
pubmed: 17407300
Chem Rev. 2006 Nov;106(11):4644-80
pubmed: 17091931
J Org Chem. 2010 Jun 18;75(12):4131-4
pubmed: 20481591
Org Lett. 2010 May 7;12(9):1976-9
pubmed: 20337490
J Am Chem Soc. 2016 Mar 30;138(12):4014-7
pubmed: 26978243
Org Lett. 2010 Dec 3;12(23):5422-5
pubmed: 21043477
Angew Chem Int Ed Engl. 2008;47(1):177-80
pubmed: 18033712
Asian J Org Chem. 2017 Jun;6(6):636-653
pubmed: 29130026
Chem Commun (Camb). 2020 Nov 7;56(86):13125-13128
pubmed: 33005910
J Am Chem Soc. 2008 Aug 6;130(31):10066-7
pubmed: 18613664
Bioorg Med Chem. 2011 Nov 15;19(22):6885-91
pubmed: 22000949
J Org Chem. 2007 Apr 27;72(9):3218-22
pubmed: 17408285
J Org Chem. 2016 Oct 7;81(19):9402-9408
pubmed: 27564224
Chem Sci. 2020 May 29;11(24):6283-6288
pubmed: 32953024
J Am Chem Soc. 2015 Aug 5;137(30):9531-4
pubmed: 26196355
Nat Commun. 2020 Dec 22;11(1):6432
pubmed: 33353940
Org Biomol Chem. 2010 May 7;8(9):2020-7
pubmed: 20401377
Chem Pharm Bull (Tokyo). 2005 Nov;53(11):1502-7
pubmed: 16272743
J Am Chem Soc. 2021 Mar 17;143(10):3747-3752
pubmed: 33651598
Org Lett. 2017 Apr 7;19(7):1734-1737
pubmed: 28294624
Org Lett. 2017 Jan 20;19(2):308-311
pubmed: 28045266
Org Biomol Chem. 2019 Sep 25;17(37):8467-8485
pubmed: 31498368
Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11444-11448
pubmed: 31197921
Org Lett. 2013 Jul 5;15(13):3338-41
pubmed: 23782427
Org Lett. 2010 Jul 16;12(14):3140-3
pubmed: 20550215
Chem Commun (Camb). 2017 Oct 31;53(87):11873-11876
pubmed: 29043306
Org Lett. 2017 Apr 7;19(7):1674-1677
pubmed: 28345930