The key role of R-NHC coupling (R = C, H, heteroatom) and M-NHC bond cleavage in the evolution of M/NHC complexes and formation of catalytically active species.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
21 Jul 2020
21 Jul 2020
Historique:
received:
09
05
2020
accepted:
19
06
2020
entrez:
2
11
2020
pubmed:
3
11
2020
medline:
3
11
2020
Statut:
epublish
Résumé
Complexes of metals with N-heterocyclic carbene ligands (M/NHC) are typically considered the systems of choice in homogeneous catalysis due to their stable metal-ligand framework. However, it becomes obvious that even metal species with a strong M-NHC bond can undergo evolution in catalytic systems, and processes of M-NHC bond cleavage are common for different metals and NHC ligands. This review is focused on the main types of the M-NHC bond cleavage reactions and their impact on activity and stability of M/NHC catalytic systems. For the first time, we consider these processes in terms of NHC-connected and NHC-disconnected active species derived from M/NHC precatalysts and classify them as fundamentally different types of catalysts. Problems of rational catalyst design and sustainability issues are discussed in the context of the two different types of M/NHC catalysis mechanisms.
Identifiants
pubmed: 33133486
doi: 10.1039/d0sc02629h
pii: d0sc02629h
pmc: PMC7553045
doi:
Types de publication
Journal Article
Review
Langues
eng
Pagination
6957-6977Informations de copyright
This journal is © The Royal Society of Chemistry 2020.
Références
Inorg Chem. 2014 Oct 6;53(19):10578-84
pubmed: 25203858
Dalton Trans. 2014 Oct 14;43(38):14346-58
pubmed: 24920060
Chemistry. 2018 Sep 25;24(54):14392-14399
pubmed: 30004600
Chem Rev. 2012 Mar 14;112(3):1536-54
pubmed: 22023323
J Am Chem Soc. 2001 May 2;123(17):4029-40
pubmed: 11457154
Chemistry. 2015 Dec 1;21(49):17610-3
pubmed: 26482554
Inorg Chem. 2007 Mar 19;46(6):1865-75
pubmed: 17348717
Chemistry. 2018 Dec 17;24(71):18922-18932
pubmed: 30357989
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7470-7474
pubmed: 28481013
Chem Commun (Camb). 2010 Apr 14;46(14):2480-2
pubmed: 20309474
Inorg Chem. 2019 Jun 3;58(11):7634-7644
pubmed: 31083985
Chem Rev. 2018 Mar 14;118(5):2636-2679
pubmed: 28975795
J Am Chem Soc. 2018 Oct 3;140(39):12566-12573
pubmed: 30168716
Angew Chem Int Ed Engl. 2012 Nov 5;51(45):11354-7
pubmed: 23038603
Chemistry. 2019 Apr 11;25(21):5472-5479
pubmed: 30693990
Angew Chem Int Ed Engl. 2009;48(28):5182-6
pubmed: 19526472
Inorg Chem. 2005 May 30;44(11):3774-6
pubmed: 15907100
Chem Rev. 2018 Oct 10;118(19):9988-10031
pubmed: 28151645
Chem Rev. 2019 Mar 27;119(6):3730-3961
pubmed: 30843688
Org Lett. 2005 Apr 28;7(9):1857-60
pubmed: 15844924
Dalton Trans. 2007 Nov 7;(41):4650-8
pubmed: 17940645
Chem Commun (Camb). 2017 Feb 28;53(18):2650-2660
pubmed: 28203667
Angew Chem Int Ed Engl. 2005 Sep 5;44(35):5705-9
pubmed: 16059961
Angew Chem Int Ed Engl. 2013 Apr 22;52(17):4664-7
pubmed: 23520038
Chem Rev. 2018 Oct 10;118(19):9457-9492
pubmed: 29601194
Chemistry. 2013 Dec 16;19(51):17358-68
pubmed: 24243804
Org Lett. 2019 May 17;21(10):3572-3575
pubmed: 31058508
Dalton Trans. 2010 Feb 14;39(6):1444-6
pubmed: 20104298
Chem Rev. 2018 Oct 10;118(19):9843-9929
pubmed: 29847935
Chemistry. 2014 Oct 13;20(42):13716-21
pubmed: 25212827
Chemistry. 2017 Sep 27;23(54):13435-13444
pubmed: 28752935
Dalton Trans. 2009 Sep 21;(35):6930-3
pubmed: 20449132
Dalton Trans. 2009 Sep 21;(35):7099-112
pubmed: 20449154
Angew Chem Int Ed Engl. 2003 Aug 11;42(31):3690-3
pubmed: 12916049
J Am Chem Soc. 2008 May 28;130(21):6848-58
pubmed: 18444623
Chem Rev. 2019 Feb 27;119(4):2192-2452
pubmed: 30480438
Angew Chem Int Ed Engl. 2007;46(16):2768-813
pubmed: 17410611
Inorg Chem. 2011 Mar 21;50(6):2501-6
pubmed: 21319776
Chemistry. 2020 May 12;26(27):5927-5941
pubmed: 31981386
Angew Chem Int Ed Engl. 2019 Nov 25;58(48):17118-17129
pubmed: 31166642
J Am Chem Soc. 2018 Mar 14;140(10):3551-3554
pubmed: 29470082
Chem Commun (Camb). 2017 Mar 25;53(24):3489-3492
pubmed: 28280834
Angew Chem Int Ed Engl. 2004 Jul 19;43(29):3845-7
pubmed: 15258952
Organometallics. 2010 Sep 13;29(17):3683-3685
pubmed: 21116469
J Org Chem. 2017 Oct 20;82(20):10898-10911
pubmed: 28925697
J Am Chem Soc. 2008 Feb 27;130(8):2493-500
pubmed: 18251465
Dalton Trans. 2018 Dec 18;48(1):58-64
pubmed: 30403248
Nature. 2014 Jun 26;510(7506):485-96
pubmed: 24965649
J Org Chem. 2015 Aug 7;80(15):7666-73
pubmed: 26161731
Chemistry. 2013 Nov 25;19(48):16196-9
pubmed: 24174170
J Am Chem Soc. 2002 Nov 27;124(47):13964-5
pubmed: 12440873
Chem Commun (Camb). 2014 Dec 14;50(96):15159-62
pubmed: 25331451
Chemistry. 2014 Nov 24;20(48):15790-8
pubmed: 25303733
Chemistry. 2018 Jul 20;24(41):10541-10549
pubmed: 29750849
J Am Chem Soc. 2004 Dec 22;126(50):16322-3
pubmed: 15600324
Inorg Chem. 2015 May 18;54(10):4603-10
pubmed: 25938547
Chem Rev. 2017 Feb 8;117(3):1970-2058
pubmed: 28085269
J Comput Chem. 2019 Jan 5;40(1):191-199
pubmed: 30284292
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3314-32
pubmed: 22287485
J Am Chem Soc. 2013 Jun 26;135(25):9263-6
pubmed: 23731462
Dalton Trans. 2018 Aug 21;47(31):10429-10433
pubmed: 29995054
Angew Chem Int Ed Engl. 2019 Sep 16;58(38):13360-13364
pubmed: 31353768
Chemistry. 2009 Jul 20;15(29):7063-73
pubmed: 19575424
J Org Chem. 2013 Sep 20;78(18):9303-8
pubmed: 23937148
Chemistry. 2015 Oct 19;21(43):15263-71
pubmed: 26471441
Dalton Trans. 2014 Oct 14;43(38):14211-4
pubmed: 24934096
J Am Chem Soc. 2013 Mar 27;135(12):4588-91
pubmed: 23316939
Chemistry. 2017 Oct 4;23(55):13792-13801
pubmed: 28744934
J Am Chem Soc. 2013 Sep 11;135(36):13338-41
pubmed: 23978294
Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2727-9
pubmed: 24482040
Chem Rev. 2019 Apr 24;119(8):4986-5056
pubmed: 30938514
Chem Rev. 2015 Jan 14;115(1):127-50
pubmed: 25493420
Dalton Trans. 2009 Sep 21;(35):6915-23
pubmed: 20449129
Dalton Trans. 2014 Jan 7;43(1):34-7
pubmed: 24162511
Chem Soc Rev. 2017 Aug 14;46(16):4845-4854
pubmed: 28660958
Angew Chem Int Ed Engl. 2010 Sep 17;49(39):6940-52
pubmed: 20715233
Chemistry. 2020 Apr 9;26(21):4861-4865
pubmed: 32196778
Inorg Chem. 2009 Jan 19;48(2):621-7
pubmed: 19138143
Chemistry. 2013 Feb 18;19(8):2749-56
pubmed: 23296748
J Am Chem Soc. 2004 Nov 24;126(46):15195-201
pubmed: 15548016
Angew Chem Int Ed Engl. 2018 Apr 23;57(18):4981-4985
pubmed: 29498168
J Am Chem Soc. 2001 Aug 29;123(34):8317-28
pubmed: 11516281
Dalton Trans. 2017 Dec 19;47(1):112-119
pubmed: 29188837
Nat Rev Chem. 2017;1:
pubmed: 29034333
Dalton Trans. 2016 Apr 14;45(14):5941-4
pubmed: 26605692
Chem Rev. 2011 Mar 9;111(3):2177-250
pubmed: 21391570
Angew Chem Int Ed Engl. 2011 Feb 7;50(6):1359-62
pubmed: 21290512
Chem Soc Rev. 2017 Feb 6;46(3):632-733
pubmed: 28083579
Adv Colloid Interface Sci. 2016 Apr;230:13-28
pubmed: 26329594
Chem Commun (Camb). 2014 Dec 18;50(97):15313-5
pubmed: 25347320
Chemistry. 2015 Dec 1;21(49):17860-9
pubmed: 26486319
Chem Rev. 2018 Oct 10;118(19):9642-9677
pubmed: 29939023
J Org Chem. 2013 Nov 15;78(22):11117-25
pubmed: 24180285
Dalton Trans. 2017 Jun 20;46(24):7791-7799
pubmed: 28590484
Inorg Chem. 2010 Mar 15;49(6):3011-8
pubmed: 20143789
Dalton Trans. 2011 Mar 28;40(12):3074-6
pubmed: 21327287
Chem Commun (Camb). 2014 Dec 11;50(95):14926-37
pubmed: 25155373
Angew Chem Int Ed Engl. 2015 Oct 12;54(42):12236-73
pubmed: 26436516
Angew Chem Int Ed Engl. 2016 Oct 10;55(42):13306-13311
pubmed: 27655011
Chemistry. 2014 Sep 26;20(40):12729-33
pubmed: 25146112
Acc Chem Res. 2017 Sep 19;50(9):2244-2253
pubmed: 28837317
Dalton Trans. 2008 Dec 21;(47):6676-85
pubmed: 19153614
Angew Chem Int Ed Engl. 2005 Mar 18;44(13):2026-9
pubmed: 15726564
Chem Soc Rev. 2011 Oct;40(10):5151-69
pubmed: 21731956
Chemistry. 2010 May 10;16(18):5408-15
pubmed: 20373306
Inorg Chem. 2019 Sep 16;58(18):12218-12227
pubmed: 31448903
Angew Chem Int Ed Engl. 2018 Jan 8;57(2):431-436
pubmed: 29152826
Dalton Trans. 2014 Mar 21;43(11):4251-4
pubmed: 24301315
Inorg Chem. 2014 Nov 3;53(21):11447-56
pubmed: 25337998
Chemistry. 2015 Dec 1;21(49):17959-72
pubmed: 26482013
Chemistry. 2019 Dec 20;25(72):16564-16572
pubmed: 31461192
Angew Chem Int Ed Engl. 2002 Apr 15;41(8):1290-309
pubmed: 19750753
Chem Rev. 2018 Feb 28;118(4):2249-2295
pubmed: 29460627
J Am Chem Soc. 2001 Mar 21;123(11):2685-6
pubmed: 11456947
Chem Commun (Camb). 2018 Dec 20;55(2):222-225
pubmed: 30525155
Chem Rev. 2009 Aug;109(8):3612-76
pubmed: 19588961
Top Curr Chem (Cham). 2017 Aug;375(4):65
pubmed: 28589266
Chem Commun (Camb). 2019 Jul 9;55(56):8087-8089
pubmed: 31231726
Chem Commun (Camb). 2019 Jun 6;55(47):6791-6794
pubmed: 31120459
Angew Chem Int Ed Engl. 2005 Aug 19;44(33):5282-4
pubmed: 16037994
Dalton Trans. 2017 Sep 28;46(36):12027-12031
pubmed: 28853488
Acc Chem Res. 2014 Feb 18;47(2):494-503
pubmed: 24215156
Beilstein J Org Chem. 2012;8:1637-43
pubmed: 23209496
Dalton Trans. 2018 Mar 28;47(12):4267-4272
pubmed: 29487924
J Am Chem Soc. 2017 Jul 12;139(27):9144-9147
pubmed: 28635251
Chemistry. 2009 Sep 21;15(37):9375-86
pubmed: 19655345
Chemistry. 2014 Dec 22;20(52):17272-6
pubmed: 25414140
Chem Sci. 2018 Jun 6;9(25):5564-5577
pubmed: 30061988
Chemistry. 2015 Mar 2;21(10):3906-9
pubmed: 25611197
Dalton Trans. 2019 Dec 7;48(45):17052-17062
pubmed: 31696883
Chem Sci. 2015 Oct 1;6(10):5719-5728
pubmed: 29910864
Chem Rev. 2018 Oct 10;118(19):9678-9842
pubmed: 29969239
J Am Chem Soc. 2006 Mar 29;128(12):4101-11
pubmed: 16551119
Chem Commun (Camb). 2017 Feb 16;53(15):2402-2405
pubmed: 28174775
ACS Catal. 2020 Jun 5;10(11):6309-6317
pubmed: 32551183
Angew Chem Int Ed Engl. 2014 Jun 16;53(25):6482-6
pubmed: 24801592