1,2-Difunctionalizations of alkynes entailing concomitant C-C and C-N bond-forming carboamination reactions.


Journal

RSC advances
ISSN: 2046-2069
Titre abrégé: RSC Adv
Pays: England
ID NLM: 101581657

Informations de publication

Date de publication:
16 Feb 2022
Historique:
received: 03 09 2021
accepted: 30 01 2022
entrez: 15 4 2022
pubmed: 16 4 2022
medline: 16 4 2022
Statut: epublish

Résumé

Vicinal carboamination of alkynes is a highly reliable and efficient practical strategy for the quick preparation of valuable and diverse amine derivatives starting from simple synthons. The last decade has witnessed numerous practical methods employing transition-metal-based/metal-free carboamination approaches using alkynes for the synthesis of these N-bearing entities. Driven by the renaissance of transition metal catalysis, intermolecular and intramolecular carboamination of alkynes comprising concomitant C-N and C-C bond formation has been studied extensively. In contrast to metal catalysis, though analogous metal-free approaches have been relatively less explored in the literature, they serve as alternatives to these expensive approaches. Despite this significant progress, reviews documenting such examples are sporadic; as a result, most reports of this type remained scattered throughout the literature, thereby hampering further developments in this escalating field. In this review, different conceptual approaches will be discussed and examples from the literature will be presented. Further, the reader will get insight into the mechanisms of different transformations.

Identifiants

pubmed: 35424576
doi: 10.1039/d1ra06633a
pii: d1ra06633a
pmc: PMC8981577
doi:

Types de publication

Journal Article Review

Langues

eng

Pagination

5847-5870

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

There are no conflicts to declare.

Références

Angew Chem Int Ed Engl. 2011 Jul 4;50(28):6379-82
pubmed: 21612009
Angew Chem Int Ed Engl. 2014 Sep 15;53(38):10209-12
pubmed: 25060365
Chem Commun (Camb). 2017 Feb 16;53(15):2386-2389
pubmed: 28174767
Org Lett. 2014 Sep 19;16(18):4830-3
pubmed: 25203435
Chem Commun (Camb). 2020 Sep 22;56(75):11070-11073
pubmed: 32812560
J Am Chem Soc. 2020 Oct 14;142(41):17306-17311
pubmed: 32981319
Chem Commun (Camb). 2017 Mar 25;53(24):3481-3484
pubmed: 28276553
European J Org Chem. 2007 Feb;2007(4):571-582
pubmed: 20577649
Org Lett. 2014 Oct 17;16(20):5354-7
pubmed: 25275617
Org Lett. 2010 Jul 16;12(14):3279-81
pubmed: 20568827
J Am Chem Soc. 2004 Sep 1;126(34):10546-7
pubmed: 15327305
Nat Chem. 2016 Jan;8(1):63-8
pubmed: 26673265
J Org Chem. 2015 Mar 6;80(5):2835-41
pubmed: 25686292
J Am Chem Soc. 2009 Sep 2;131(34):12050-1
pubmed: 19705909
Org Lett. 2019 Dec 20;21(24):9841-9845
pubmed: 31829020
Org Lett. 2011 Mar 4;13(5):1206-9
pubmed: 21302974
J Org Chem. 2015 Sep 18;80(18):9307-13
pubmed: 26305915
Org Lett. 2010 Dec 3;12(23):5426-9
pubmed: 21038875
J Org Chem. 2020 Dec 4;85(23):14937-14944
pubmed: 33146531
Org Lett. 2008 Jul 17;10(14):3085-8
pubmed: 18558759
J Org Chem. 2019 Apr 5;84(7):4120-4130
pubmed: 30813732
Org Lett. 2019 Mar 15;21(6):1779-1783
pubmed: 30829037
Chemistry. 2016 Apr 18;22(17):5899-903
pubmed: 26951887
Angew Chem Int Ed Engl. 2020 Jun 26;59(27):11130-11135
pubmed: 32129528
J Am Chem Soc. 2011 Sep 28;133(38):14952-5
pubmed: 21875095
Org Lett. 2019 Jul 19;21(14):5421-5425
pubmed: 31251634
Acc Chem Res. 2020 Jan 21;53(1):84-104
pubmed: 31854967
Org Lett. 2019 Oct 18;21(20):8364-8368
pubmed: 31584826
Org Lett. 2019 Jun 7;21(11):4250-4254
pubmed: 31124689
J Am Chem Soc. 2016 Nov 9;138(44):14570-14573
pubmed: 27790910
Org Lett. 2014 Jul 3;16(13):3476-9
pubmed: 24964008
Angew Chem Int Ed Engl. 2004 Oct 11;43(40):5372-4
pubmed: 15468090
J Am Chem Soc. 2008 May 14;130(19):6058-9
pubmed: 18412348
Org Lett. 2017 Jul 7;19(13):3474-3477
pubmed: 28621545
Angew Chem Int Ed Engl. 2009;48(25):4572-6
pubmed: 19444850
J Org Chem. 2017 Feb 17;82(4):2067-2080
pubmed: 28106403
Org Lett. 2012 Jul 6;14(13):3478-81
pubmed: 22691052
Org Lett. 2012 Jun 15;14(12):3032-5
pubmed: 22646751
J Org Chem. 2017 May 19;82(10):5068-5079
pubmed: 28470065
Chem Soc Rev. 2018 Oct 29;47(21):7926-7953
pubmed: 29993045
Org Lett. 2018 Sep 7;20(17):5103-5106
pubmed: 30106589
Org Lett. 2010 Dec 17;12(24):5688-91
pubmed: 21082771
J Am Chem Soc. 2005 Sep 28;127(38):13112-3
pubmed: 16173716
Chem Asian J. 2011 Feb 1;6(2):359-62
pubmed: 21254411
Org Lett. 2012 Dec 21;14(24):6318-21
pubmed: 23234384
Isr J Chem. 2020 Mar;60(3-4):219-229
pubmed: 33785969
Asian J Org Chem. 2017 Jun;6(6):636-653
pubmed: 29130026
Org Lett. 2018 Jan 5;20(1):220-223
pubmed: 29219320
Org Lett. 2012 Feb 3;14(3):764-7
pubmed: 22242646
Angew Chem Int Ed Engl. 2015 Jun 26;54(27):7862-6
pubmed: 26012899
Org Biomol Chem. 2017 Oct 31;15(42):8904-8913
pubmed: 28994844
Chem Soc Rev. 2020 Mar 21;49(6):1790-1811
pubmed: 32055811
Org Lett. 2016 May 6;18(9):2200-3
pubmed: 27119774
J Org Chem. 2019 Sep 6;84(17):10843-10851
pubmed: 31385504
J Org Chem. 2003 Feb 7;68(3):920-8
pubmed: 12558417
Org Lett. 2010 May 7;12(9):2068-71
pubmed: 20377234
J Org Chem. 2016 Aug 5;81(15):6563-72
pubmed: 27380814
Org Biomol Chem. 2012 Dec 21;10(47):9429-39
pubmed: 23108795
J Organomet Chem. 2011 Jan 1;696(1):150-158
pubmed: 21379363
Chem Commun (Camb). 2016 Apr 28;52(33):5761-4
pubmed: 27049140
Org Lett. 2015 Dec 18;17(24):6250-3
pubmed: 26649487
Org Lett. 2018 Jun 15;20(12):3477-3481
pubmed: 29863361
Org Lett. 2010 Jul 2;12(13):2908-11
pubmed: 20515016
J Org Chem. 2012 Oct 19;77(20):9190-8
pubmed: 22978404
Org Lett. 2020 Nov 6;22(21):8550-8554
pubmed: 33104355
J Org Chem. 2013 Jun 7;78(11):5254-63
pubmed: 23650873
J Org Chem. 2002 Oct 4;67(20):7042-7
pubmed: 12353998
Chem Rec. 2018 Sep;18(9):1314-1340
pubmed: 29517841
Org Lett. 2019 Dec 6;21(23):9415-9419
pubmed: 31742412
Org Lett. 2020 Jun 5;22(11):4350-4354
pubmed: 32412769
J Am Chem Soc. 2009 Jun 10;131(22):7494-5
pubmed: 19435347
Chemistry. 2020 May 4;26(25):5607-5610
pubmed: 32045038

Auteurs

Santosh Kumar Nanda (SK)

Department of Chemistry, School of Applied Science, Centurion University of Technology and Management Paralakhemundi Odisha-761211 India sknanda@cutm.ac.in.

Rosy Mallik (R)

Department of Chemistry, School of Applied Science, Centurion University of Technology and Management Paralakhemundi Odisha-761211 India sknanda@cutm.ac.in.

Classifications MeSH