Carbodiimide and Isocyanate Hydroboration by a Cyclic Carbodiphosphorane Catalyst.
Lewis bases
carbodiphosphorane
hydroboration
organocatalysis
zerovalent carbon
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
17 Oct 2023
17 Oct 2023
Historique:
received:
23
09
2023
pubmed:
17
10
2023
medline:
17
10
2023
entrez:
17
10
2023
Statut:
aheadofprint
Résumé
We report hydroboration of carbodiimide and isocyanate substrates catalyzed by a cyclic carbodiphosphorane catalyst. The cyclic carbodiphosphorane outperformed the other Lewis basic carbon species tested, including other zerovalent carbon compounds, phosphorus ylides, an N-heterocyclic carbene, and an N-heterocyclic olefin. Hydroborations of seven carbodiimides and nine isocyanates were performed at room temperature to form N-boryl formamidine and N-boryl formamide products. Intermolecular competition experiments demonstrated the selective hydroboration of alkyl isocyanates over carbodiimide and ketone substrates. DFT calculations support a proposed mechanism involving activation of pinacolborane by the carbodiphosphorane catalyst, followed by hydride transfer and B-N bond formation.
Identifiants
pubmed: 37847813
doi: 10.1002/chem.202303095
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303095Subventions
Organisme : American Chemical Society Petroleum Research Fund
ID : 62239-UNI1
Organisme : Division of Chemistry
ID : CHE-2213507
Organisme : Organic Syntheses, Inc.
Organisme : Chapman University
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
R. M. Hollingworth, Environ. Health Perspect. 1976, 13.
P. D. Evans, J. D. Gee, Nature 1980, 287, 60-62.
J. Pouessel, O. Jacquet, T. Cantat, ChemCatChem 2013, 5, 3552-3556.
T. M. E. Dine, D. Evans, J. Rouden, J. Blanchet, Chem. Eur. J. 2016, 22, 5894-5898.
K. Kaji, H. Matsubara, H. Nagashima, Y. Kikugawa, S. Yamada, Chem. Pharm. Bull. 1978, 26, 2246-2249.
T. Peddarao, A. Baishya, M. K. Barman, A. Kumar, S. Nembenna, New J. Chem. 2016, 40, 7627-7636.
V. Pace, K. de la Vega-Hernández, E. Urban, T. Langer, Org. Lett. 2016, 18, 2750-2753.
C. Weetman, M. S. Hill, M. F. Mahon, Chem. Eur. J. 2016, 22, 7158-7162.
D. Mukherjee, S. Shirase, T. P. Spaniol, K. Mashima, J. Okuda, Chem. Commun. 2016, 52, 13155-13158.
M. Khononov, N. Fridman, M. Tamm, M. S. Eisen, Eur. J. Org. Chem. 2020, 2020, 3153-3160.
P. Ghosh, A. Jacobi Von Wangelin, Angew. Chem. Int. Ed. 2021, 60, 16035-16043.
L. E. English, T. M. Horsley Downie, C. L. Lyall, M. F. Mahon, C. L. McMullin, S. E. Neale, C. M. Saunders, D. J. Liptrot, Chem. Commun. 2023, 59, 1074-1077.
M. D. Anker, M. Arrowsmith, R. L. Arrowsmith, M. S. Hill, M. F. Mahon, Inorg. Chem. 2017, 56, 5976-5983.
M. Rauch, S. Ruccolo, G. Parkin, J. Am. Chem. Soc. 2017, 139, 13264-13267.
A. Ramos, A. Antiñolo, F. Carrillo-Hermosilla, R. Fernández-Galán, D. García-Vivó, Chem. Commun. 2019, 55, 3073-3076.
Q. Shen, X. Ma, W. Li, W. Liu, Y. Ding, Z. Yang, H. W. Roesky, Chem. Eur. J. 2019, 25, 11918-11923.
Y. Ding, X. Ma, Y. Liu, W. Liu, Z. Yang, H. W. Roesky, Organometallics 2019, 38, 3092-3097.
N. Sarkar, S. Bera, S. Nembenna, J. Org. Chem. 2020, 85, 4999-5009.
T. K. Panda, I. Banerjee, S. Sagar, Appl. Organomet. Chem. 2020, 34, e5765.
X. He, B. Yan, C. Ni, Y. Zhao, Z. Yang, X. Ma, Asian J. Org. Chem. 2021, 10, 196-201.
M. K. Bisai, K. Gour, T. Das, K. Vanka, S. S. Sen, J. Organomet. Chem. 2021, 949, 121924.
B. Yan, X. He, C. Ni, Z. Yang, X. Ma, ChemCatChem 2021, 13, 851-854.
B. L. L. Réant, B. Van IJzendoorn, G. F. S. Whitehead, M. Mehta, Dalton Trans. 2022, 51, 18329-18336.
N. Sarkar, R. K. Sahoo, S. Nembenna, Eur. J. Org. Chem. 2022, ejoc.202200941.
B. Van IJzendoorn, S. F. Albawardi, I. J. Vitorica-Yrezabal, G. F. S. Whitehead, J. E. McGrady, M. Mehta, J. Am. Chem. Soc. 2022, 144, 21213-21223.
S. E. Prey, C. Herok, F. Fantuzzi, M. Bolte, H.-W. Lerner, B. Engels, M. Wagner, Chem. Sci. 2023, 14, 849-860.
R. K. Sahoo, A. G. Patro, N. Sarkar, S. Nembenna, Organometallics 2023, 42, 1746-1758.
H. Liu, K. Kulbitski, M. Tamm, M. S. Eisen, Chem. Eur. J. 2018, 24, 5738-5742.
Y. Yang, M. D. Anker, J. Fang, M. F. Mahon, L. Maron, C. Weetman, M. S. Hill, Chem. Sci. 2017, 8, 3529-3537.
R. K. Sahoo, N. Sarkar, S. Nembenna, Angew. Chem. Int. Ed. 2021, 60, 11991-12000.
Q. Xiao, S. Zang, Z. Chen, W. Yao, J. Zheng, M. Ma, Chin. J. Org. Chem. 2021, 41, 357-363.
Z. Du, B. Behera, A. Kumar, Y. Ding, J. Organomet. Chem. 2021, 950, 121982.
V. K. Pandey, S. Sahoo, A. Rit, Chem. Commun. 2022, 58, 5514-5517.
C. Ni, X. Ma, Z. Yang, H. W. Roesky, ChemistrySelect 2022, 7, e202202878.
K. A. Gudun, S. Tussupbayev, A. Slamova, A. Y. Khalimon, Org. Biomol. Chem. 2022, 20, 6821-6830.
J. Shi, M. Luo, X. Zhang, T. Yuan, X. Chen, M. Ma, Org. Biomol. Chem. 2023, 21, 3628-3635.
K. Makarov, I. Ritacco, N. Fridman, L. Caporaso, M. S. Eisen, ACS Catal. 2023, 11798-11814.
Y.-C. Teo, D. Loh, B.-X. Leong, Z.-F. Zhang, M.-D. Su, C.-W. So, Inorg. Chem. 2023, acs.inorgchem.3c02424.
S. Ostrowska, P. Arnaut, D. J. Liptrot, C. S. J. Cazin, S. P. Nolan, Chem. Commun. 2023, 59, 9126-9129.
R. Kumar, V. Sharma, S. Banerjee, K. Vanka, S. S. Sen, Chem. Commun. 2023, 59, 2255-2258.
D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-92.
P. de Frémont, N. Marion, S. P. Nolan, Coord. Chem. Rev. 2009, 253, 862-892.
P. Bellotti, M. Koy, M. N. Hopkinson, F. Glorius, Nat. Chem. Rev. 2021, 5, 711-725.
S. Kumar Kushvaha, A. Mishra, H. W. Roesky, K. Chandra Mondal, Chem. Asian J. 2022, 17, e202101301.
C. A. Smith, M. R. Narouz, P. A. Lummis, I. Singh, A. Nazemi, C.-H. Li, C. M. Crudden, Chem. Rev. 2019, 119, 4986-5056.
H. Shen, G. Tian, Z. Xu, L. Wang, Q. Wu, Y. Zhang, B. K. Teo, N. Zheng, Coord. Chem. Rev. 2022, 458, 214425.
C. S. J. Cazin, N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis, Springer, Dordrecht; New York, 2011.
S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676.
C. Chen, F. Liu, M. Szostak, Chem. Eur. J. 2021, 27, 4478-4499.
A. T. Biju, N-Heterocyclic Carbenes in Organocatalysis, Wiley-VCH, Weinheim, 2019.
D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606-5655.
S. J. Ryan, L. Candish, D. W. Lupton, Chem. Soc. Rev. 2013, 42, 4906-4917.
S. Dwivedi, S. Gupta, S. Das, COCAT 2014, 1, 13-39.
D. M. Flanigan, F. Romanov-Michailidis, N. A. White, T. Rovis, Chem. Rev. 2015, 115, 9307-9387.
G. Frenking, R. Tonner, Pure Appl. Chem. 2009, 81, 597-614.
M. Fustier-Boutignon, N. Nebra, N. Mézailles, Chem. Rev. 2019, 119, 8555-8700.
W. Petz, G. Frenking, in Transition Metal Complexes of Neutral Eta1-Carbon Ligands (Eds.: R. Chauvin, Y. Canac), Springer Berlin Heidelberg, Berlin, Heidelberg, 2010, pp. 49-92.
M. Alcarazo, in Modern Ylide Chemistry (Ed.: V. H. Gessner), Springer International Publishing, Cham, 2017, pp. 25-50.
T.-H. Wang, W.-C. Chen, T.-G. Ong, J. Chin. Chem. Soc. 2017, 64, 124-132.
S. Liu, W.-C. Shih, W.-C. Chen, T.-G. Ong, ChemCatChem 2018, 10, 1483-1498.
L. Zhao, C. Chai, W. Petz, G. Frenking, Molecules 2020, 25, 4943.
R. Dobrovetsky, D. W. Stephan, Angew. Chem. Int. Ed. 2013, 52, 2516-2519.
W.-C. Chen, J.-S. Shen, T. Jurca, C.-J. Peng, Y.-H. Lin, Y.-P. Wang, W.-C. Shih, G. P. A. Yap, T.-G. Ong, Angew. Chem. Int. Ed. 2015, 54, 15207-15212.
Y. Chan, Y. Bai, W. Chen, H. Chen, C. Li, Y. Wu, M. Tseng, G. P. A. Yap, L. Zhao, H. Chen, T. Ong, Angew. Chem. Int. Ed. 2021, 60, 19949-19956.
C. R. Aversa-Fleener, D. K. Chang, A. L. Liberman-Martin, Organometallics 2021, 40, 4050-4054.
A. L. Liberman-Martin, Cell Reports Physical Science 2023, 101519.
F. Ramirez, N. B. Desai, B. Hansen, N. McKelvie, J. Am. Chem. Soc. 1961, 83, 3539-3540.
C. Zybill, G. Mueller, Organometallics 1987, 6, 2489-2494.
C. Pranckevicius, D. A. Iovan, D. W. Stephan, Dalton Trans. 2016, 45, 16820-16825.
M. Gruber, W. Bauer, H. Maid, K. Schöll, R. R. Tykwinski, Inorg. Chim. Acta 2017, 468, 152-158.
M. S. Hussain, H. Schmidbaur, Z. Naturforsch. B 1976, 31, 721-726.
H. Schmidbaur, T. Costa, B. Milewski-Mahrla, U. Schubert, Angew. Chem. Int. Ed. Engl. 1980, 19, 555-556.
S. Liu, W.-C. Chen, G. P. A. Yap, T.-G. Ong, Organometallics 2020, 39, 4395-4401.
C. A. Dyker, V. Lavallo, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2008, 47, 3206-3209.
H. A. Duong, M. J. Cross, J. Louie, Org. Lett. 2004, 6, 4679-4681.
C. Li, W. Zhao, J. He, Y. Zhang, Chem. Commun. 2019, 55, 12563-12566.
S. M. Raders, J. G. Verkade, J. Org. Chem. 2010, 75, 5308-5311.
W. L. Jorgensen, J. Tirado-Rives, J. Am. Chem. Soc. 1988, 110, 1657-1666.
Schrödinger. Schrödinger Release 2021-3: Macromodel; Schrödinger, LLC: New York, NY, 2021.
J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615-6620.
J.-D. Chai, M. Head-Gordon, J. Chem. Phys. 2008, 128, 084106.
J. S. Binkley, J. A. Pople, W. J. Hehre, J. Am. Chem. Soc. 1980, 102, 939-947.
M. S. Gordon, J. S. Binkley, J. A. Pople, W. J. Pietro, W. J. Hehre, J. Am. Chem. Soc. 1982, 104, 2797-2803.
V. A. Rassolov, M. A. Ratner, J. A. Pople, P. C. Redfern, L. A. Curtiss, J. Comput. Chem. 2001, 22, 976-984.
M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665.
K. Fukui, Acc. Chem. Res. 1981, 14, 363-368.
H. P. Hratchian, M. J. Frisch, J. Chem. Phys. 2011, 134, 204103.
F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835.
A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
B. Mennucci, J. Tomasi, R. Cammi, J. R. Cheeseman, M. J. Frisch, F. J. Devlin, S. Gabriel, P. J. Stephens, J. Phys. Chem. A 2002, 106, 6102-6113.
B. Mennucci, J. Tomasi, J. Chem. Phys. 1997, 106, 5151-5158.
Gaussian 16, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
R. Tonner, G. Frenking, Chem. Eur. J. 2008, 14, 3260-3272.
F. Ramirez, J. F. Pilot, N. B. Desai, C. P. Smith, B. Hansen, N. McKelvie, J. Am. Chem. Soc. 1967, 89, 6273-6276.
G. H. Birum, C. N. Matthews, Chem. Commun. 1967, 137-138.
G. Chioccola, J. J. Daly, J. Chem. Soc. A 1968, 568-577.
S. Kozuch, S. Shaik, Acc. Chem. Res. 2011, 44, 101-110.
W. J. Transue, J. Yang, M. Nava, I. V. Sergeyev, T. J. Barnum, M. C. McCarthy, C. C. Cummins, J. Am. Chem. Soc. 2018, 140, 17985-17991.
A. K. Swarnakar, S. M. McDonald, K. C. Deutsch, P. Choi, M. J. Ferguson, R. McDonald, E. Rivard, Inorg. Chem. 2014, 53, 8662-8671.
L. Hintermann, Beilstein J. Org. Chem. 2007, 3, DOI 10.1186/1860-5397-3-22.
M. Pompeo, R. D. J. Froese, N. Hadei, M. G. Organ, Angew. Chem. Int. Ed. 2012, 51, 11354-11357.
K. Powers, C. Hering-Junghans, R. McDonald, M. J. Ferguson, E. Rivard, Polyhedron 2016, 108, 8-14.
V. Ramirez, E. B. Van Pelt, R. K. Pooni, A. J. Melchor Bañales, M. B. Larsen, Org. Biomol. Chem. 2022, 20, 5861-5868.
Z. Guo, Y. Xu, X. Wu, X. Wei, C. Xi, Dalton Trans. 2019, 48, 8116-8121.