Gold-Catalysed Heck Reaction: Fact or Fiction? Correspondence on "Unlocking the Chain Walking Process in Gold Catalysis".
Heck reaction
NMR
carbocations
gold catalysis
heteroarylation
mechanisms
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:
02 May 2024
02 May 2024
Historique:
received:
24
11
2023
medline:
2
5
2024
pubmed:
2
5
2024
entrez:
2
5
2024
Statut:
aheadofprint
Résumé
Two recent high-profile publications reported the formation of Heck-type arylated alkenes catalysed by MeDalPhosAuCl/AgOTf (J. Am. Chem. Soc. 2023, 145, 8810) and their cyclisation to tetralines (Angew. Chem. Int. Ed. 2023, e202312786). It was claimed that these were the first demonstrations in gold catalysis of alkene insertion into Au-aryl bonds, β-H elimination and chain-walking by Au-H dications. We show here that in fact this chemistry is a two-stage process. Only the first step, the production of an alkyl triflate ester as the primary organic product by the well-known alkene heteroarylation sequence, involves gold. The subsequent formation of Heck-type olefins and their cyclisation to tetralines represent classical H
Identifiants
pubmed: 38695675
doi: 10.1002/anie.202317774
doi:
Types de publication
Letter
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202317774Subventions
Organisme : Royal Society of Chemistry
ID : R22-0875640255
Informations de copyright
© 2024 Wiley-VCH GmbH.
Références
R. F. Heck, J. Am. Chem. Soc. 1968, 90, 5518–5526;
Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166–7169;
T. Mizoroki, K. Mori, A. Azuki, Bull. Chem. Soc. Jpn. 1971, 44, 581;
R. F. Heck, J. P. Nolley, Jr., J. Org. Chem. 1972, 37, 2320–2322.
R. F. Heck, Acc. Chem. Res. 1979, 12, 146–151.
C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 2012, 51, 5062–5085.
L. Rocchigiani, M. Bochmann, Chem. Rev. 2021, 121, 8364–8451;
M. Joost, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2015, 54, 15022–15045.
F. Rekhroukh, R. Brousses, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2015, 54, 1266–1269;
F. Rekhroukh, L. Estevez, C. Bijani, K. Miqueu, A. Amgoune, D. Bourissou, Organometallics 2016, 35, 995–1001;
F. Rekhroukh, C. Blons, L. Estévez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, Chem. Sci. 2017, 8, 4539–4545.
F. Rekhroukh, L. Estevez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, J. Am. Chem. Soc. 2016, 138, 11920–11929.
J. Serra, P. Font, E. D. Sosa Carrizo, S. Mallet-Ladeira, S. Massou, T. Parella, K. Miqueu, A. Amgoune, X. Ribas, D. Bourissou, Chem. Sci. 2018, 9, 3932–3940.
A. Pintus, L. Rocchigiani, J. Fernandez-Cestau, P. H. M. Budzelaar, M. Bochmann, Angew. Chem. Int. Ed. 2016, 55, 12321–12324;
A. Pintus, M. Bochmann, RSC Adv. 2018, 8, 2795–2803.
G. Ung, G. Bertrand, Angew. Chem. Int. Ed. 2013, 52, 11388–11391;
G. Klatt, R. Xu, M. Pernpointner, L. Molinari, T. Q. Hung, F. Rominger, A. S. K. Hashmi, H. Köppel, Chem. Eur. J. 2013, 19, 3954–3961.
E. Y. Tsui, P Müller, J. P. Sadighi, Angew. Chem. Int. Ed. 2008, 47, 8937–8940;
D.-A. Roşca, J. Fernandez-Cestau, D. L. Hughes, M. Bochmann, Organometallics 2015, 34, 2098–2101;
D.-A. Roşca, D. A. Smith, D. L. Hughes, M. Bochmann, Angew. Chem. Int. Ed. 2012, 51, 10643–10646;
D.-A. Roşca, J. Fernandez-Cestau, J. Morris, J. A. Wright, M. Bochmann, Sci. Adv. 2015, 1, e1500761;
L. Rocchigiani, J. Fernandez–Cestau, I. Chambrier, P. Hrobarik, M. Bochmann, J. Am. Chem. Soc. 2018, 140, 8287–8302.
A. Nijamudheen, S. Karmakar, A. Datta, Chem. Eur. J. 2014, 20, 14650–14658.
N. Savjani, D.-A. Roşca, M. Schormann, M. Bochmann, Angew. Chem. Int. Ed. 2013, 52, 874–877;
E. Langseth, A. Nova, E. A. Tråseth, F. Rise, S. Øien, R. H. Heyn, M. Tilset, J. Am. Chem. Soc. 2014, 136, 10104–10115;
M. S. Martinsen Holmsen, F. S. Ihlefeldt, S. Øien-Ødegaard, E. Langseth, Y. Wencke, R. H. Heyn, M. Tilset, Organometallics 2018, 37, 1937–1947;
M. S. Martinsen Holmsen, A. Nova, D. Balcells, E. Langseth, S. Øien-Ødegaard, E. A. Tråseth, R. H. Heyn, M. Tilset, Dalton Trans. 2016, 45, 14719–14724;
D. Balcells, O. Eisenstein, M, Tilset, A. Nova, Dalton Trans. 2016, 45, 5504–5513.
G. Zhang, L. Cui, Y. Wang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 1474–1475;
A. D. Melhado, W. E. Brenzovich, A. D. Lackner, F. D. Toste, J. Am. Chem. Soc. 2010, 132, 8885–8887;
L. T. Ball, M. Green, G. C. Lloyd-Jones, C. A. Russell, Org. Lett. 2010, 12, 4724;
W. E. Brenzovich, J. F. Brazeau, F. D. Toste, Org. Lett. 2010, 12, 4728–4731;
E. Tkatchouk, N. P. Mankad, D. Benitez, W. A. Goddard, III, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 14293–14300;
L. T. Ball, G. C. Lloyd-Jones, C. A. Russell, Chem. Eur. J. 2012, 18, 2931–2937;
W. E. Brenzovich, Jr, D. Benitez, A. D. Lackner, H. P. Shunatona, E. Tkatchouk, W. A. Goddard, III, F. D. Toste, Angew. Chem. Int. Ed. 2010, 49, 5519–5522;
M. J. Harper, E. J. Emmett, J. F. Bower, C. A. Russell, J. Am. Chem. Soc. 2017, 139, 12386–12389;
M. Rigoulet, O. Thillaye du Boullay, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2020, 59, 16625–16630;
J. Rodriguez, A. Tabey, S. Mallet-Ladeira, D. Bourissou, Chem. Sci. 2021, 12, 7706–7712;
S. Zhang, C. Wang, X. Ye, X. Shi, Angew. Chem. Int. Ed. 2020, 59, 20470–20474;
A. G. U. Tathe, A. K. Yadav, C. C. Chintawar, N. T. Patil, ACS Catal. 2021, 11, 4576–4582;
C. C. Chintawar, V. W. Bhoyare, M. V. Mane, N. T. Patil, J. Am. Chem. Soc. 2022, 144, 7089–7095;
S. C. Scott, J. A. Cadge, G. K. Boden, J. F. Bower, C. A. Russell, Angew. Chem. Int. Ed. 2023, 62, e202301526.
B. Sahoo, M. N. Hopkinson, F. Glorius, J. Am. Chem. Soc. 2013, 135, 5505–5508;
M. N. Hopkinson, B. Sahoo, F. Glorius, Adv. Synth. Catal. 2014, 356, 2794–2800;
B. Dong, H. Peng, S. E. Motika, X. Shi, Chem. Eur. J. 2017, 23, 11093–11099.
V. W. Bhoyare, A. G. Tathe, A. Das, C. C. Chintawar, N. T. Patil, Chem. Soc. Rev. 2021, 50, 10422–10450.
M. Rigoulet, K. Miqueu, D. Bourissou, Chem. Eur. J. 2022, 28, e202202110.
V. W. Bhoyare, E. D. Sosa Carrizo, C. C. Chintawar, V. Gandon, N. T. Patil, J. Am. Chem. Soc. 2023, 145, 8810–8816.
V. W. Bhoyare, A. G. Tathe, V. Gandon, N. T. Patil, Angew. Chem. Int. Ed. 2023, e202312786.
C. Wei, L. Zhang, Z. Xia, Org. Lett. 2023, 25, 6808–6812.
F. E. Condon, D. L. West, J. Org. Chem. 1980, 45, 2006–2009.
A. Zeineddine, L. Estévez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, Nat. Commun. 2017, 8, 565;
J. Rodriguez, A. Zeineddine, E. D. Sosa Carrizo, K. Miqueu, N. Saffon-Merceron, A. Amgoune, D. Bourissou, Chem. Sci. 2019, 10, 7183–7192.
M. Rigoulet, S. Massou, E. D. Sosa Carrizo, S. Mallet-Ladeira, A. Amgoune, K. Miqueu, D. Bourissou, PNAS 2019, 116, 46–51.
M. Navarro, A. Toledo, S. Mallet-Ladeira, E. D. Sosa Carrizo, K. Miqueu, D. Bourissou, Chem. Sci. 2020, 11, 2750–2758.
C. Gao, C. A. Wilhelmsen, J. P. Morken, J. Org. Chem. 2023, 88, 1828–1835.
L. R. Jeffries, S. P. Cook, Org. Lett. 2014, 16, 2026–2029.
D.-A. Roşca, J. A. Wright, M. Bochmann, Dalton Trans. 2015, 44, 20785–20807.
In Patil's original catalytic conditions (dichloroethane, 80 °C) 0.7 equiv of base was found optimal, for the deprotonation of (LH)AuOTf. This leaves sufficient residual acid to initiate carbocationic reactions.
R. J. Phipps, L. McMurray, S. Ritter, H. A. Duong, M. J. Gaunt, J. Am. Chem. Soc. 2012, 134, 10773–10776.
F. Zhang, S. Das, A. J. Walkinshaw, A. Casitas, M. Taylor, M. G. Suero, M. J. Gaunt, J. Am. Chem. Soc. 2014, 136, 8851–8854.
S. J. Lancaster, A. Rodriguez, A. Lara-Sanchez, M. D. Hannant, D. A. Walker, D. L. Hughes, M. Bochmann, Organometallics 2002, 21, 451–453.