Diastereoselective Double C-H Functionalization of Chiral Ferrocenes with Heteroaromatics.
C−H activation
asymmetric catalysis
ferrocene
heterocycles
palladium
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
05 Nov 2021
05 Nov 2021
Historique:
received:
16
07
2021
pubmed:
16
9
2021
medline:
10
11
2021
entrez:
15
9
2021
Statut:
ppublish
Résumé
Diastereoselective double C-H heteroarylation of chiral ferrocenes provides valuable compounds with multiple functionalities using mild reaction conditions and simple reagents. Pd-Complexes with chiral mono-protected amino acids afforded corresponding heteroarylated ferrocenyl amines in good yields and high diastereomeric purities. In this way, a variety of indole, thiophene, pyrrole, or furan substituents were introduced to the ferrocene moiety. Furthermore, a range of relevant functional groups, for example ketone, ester, chloro, nitro, or silyl, are tolerated by this method. An alternative combination of amino acid and ferrocenyl amine configurations was leveraged to provide the complementary diastereomeric products. The products of C-H heteroarylation can be transformed into corresponding phosphines. Absolute configurations of CH-activation products were confirmed by the combination of X-ray crystallographic analysis and CD spectroscopy.
Identifiants
pubmed: 34524717
doi: 10.1002/chem.202102624
doi:
Substances chimiques
Amines
0
Amino Acids
0
Metallocenes
0
Phosphines
0
Palladium
5TWQ1V240M
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15501-15507Subventions
Organisme : vedecká grantová agentúra mšvvaš sr a sav
ID : VEGA 1/0590/19
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
A. Togni, T. Hayashi, Ferrocenes, VCH, Weinheim, 1995;
P. Štepnička, Ferrocenes: Ligands, Materials and Biomolecules, Wiley, Chichester, 2008;
L.-X. Dai, X.-L. Hou, Chiral Ferrocenes in Asymmetric Catalysis, Wiley-VCH, Weinheim, 2010.
H.-U. Blaser, M. Lotz, in Chiral Ferrocenes in Asymmetric Catalysis (Eds.: L.-X. Dai, X.-L. Hou), Wiley-VCH, Weinheim, 2010;
Š. Toma, J. Csizmadiova, M. Mečiarová, R. Šebesta, Dalton Trans. 2014, 43, 16557-16579;
M. Drusan, R. Šebesta, Tetrahedron 2014, 70, 759-786;
R. G. Arrayas, J. Adrio, J. C. Carretero, Angew. Chem. Int. Ed. 2006, 45, 7674-7715;
Angew. Chem. 2006, 118, 7836-7878;
L. Cunningham, A. Benson, P. J. Guiry, Org. Biomol. Chem. 2020, 18, 9329-9370.
W.-P. Deng, V. Snieckus, C. Metallinos, in Chiral Ferrocenes in Asymmetric Catalysis, Wiley-VCH, Weinheim, 2010, pp. 15-53.
L. A. López, E. López, Dalton Trans. 2015, 44, 10128-10135;
D.-W. Gao, Q. Gu, C. Zheng, S.-L. You, Acc. Chem. Res. 2017, 50, 351-365;
C.-X. Liu, Q. Gu, S.-L. You, Trends Chem. 2020, 2, 737-749.
B.-F. Shi, N. Maugel, Y.-H. Zhang, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 4882-4886;
Angew. Chem. 2008, 120, 4960-4964.
Q. Shao, K. Wu, Z. Zhuang, S. Qian, J.-Q. Yu, Acc. Chem. Res. 2020, 53, 833-851;
D.-W. Gao, Y.-C. Shi, Q. Gu, Z.-L. Zhao, S.-L. You, J. Am. Chem. Soc. 2013, 135, 86-89;
C. Pi, Y. Li, X. Cui, H. Zhang, Y. Han, Y. Wu, Chem. Sci. 2013, 4, 2675-2679;
D.-W. Gao, Q. Yin, Q. Gu, S.-L. You, J. Am. Chem. Soc. 2014, 136, 4841-4844;
C. Pi, X. Cui, X. Liu, M. Guo, H. Zhang, Y. Wu, Org. Lett. 2014, 16, 5164-5167;
Y.-C. Shi, R.-F. Yang, D.-W. Gao, S.-L. You, Beilstein J. Org. Chem. 2013, 9, 1891-1896.
L. Liu, A.-A. Zhang, R.-J. Zhao, F. Li, T.-J. Meng, N. Ishida, M. Murakami, W.-X. Zhao, Org. Lett. 2014, 16, 5336-5338;
S. Luo, Z. Xiong, Y. Lu, Q. Zhu, Org. Lett. 2018, 20, 1837-1840.
X. Ma, Z. Gu, RSC Adv. 2014, 4, 36241-36244;
R. Deng, Y. Huang, X. Ma, G. Li, R. Zhu, B. Wang, Y.-B. Kang, Z. Gu, J. Am. Chem. Soc. 2014, 136, 4472-4475;
D.-W. Gao, Y. Gu, S.-B. Wang, Q. Gu, S.-L. You, Organometallics 2016, 35, 3227-3233;
B.-B. Xu, J. Ye, Y. Yuan, W.-L. Duan, ACS Catal. 2018, 8, 11735-11740.
T. Shibata, T. Shizuno, Angew. Chem. Int. Ed. 2014, 53, 5410-5413;
Angew. Chem. 2014, 126, 5514-5517;
T. Shibata, N. Uno, T. Sasaki, K. S. Kanyiva, J. Org. Chem. 2016, 81, 6266-6272;
D. Schmiel, R. Gathy, H. Butenschön, Organometallics 2018, 37, 2095-2110;
D. Schmiel, H. Butenschön, Eur. J. Org. Chem. 2017, 3041-3048;
A. Urbano, G. Hernandez-Torres, A. M. del Hoyo, A. Martinez-Carrion, M. Carmen Carreno, Chem. Commun. 2016, 52, 6419-6422;
E. López, J. Borge, L. A. López, Chem. Eur. J. 2017, 23, 3091-3097;
T. Shibata, T. Shizuno, T. Sasaki, Chem. Commun. 2015, 51, 7802-7804;
M. Murai, K. Matsumoto, Y. Takeuchi, K. Takai, Org. Lett. 2015, 17, 3102-3105;
Q.-W. Zhang, K. An, L.-C. Liu, Y. Yue, W. He, Angew. Chem. Int. Ed. 2015, 54, 6918-6921;
Angew. Chem. 2015, 127, 7022-7025;
S.-B. Wang, Q. Gu, S.-L. You, Organometallics 2017, 36, 4359-4362;
S.-B. Wang, Q. Gu, S.-L. You, J. Org. Chem. 2017, 82, 11829-11835;
W.-J. Kong, Q. Shao, M.-H. Li, Z.-L. Zhou, H. Xu, H.-X. Dai, J.-Q. Yu, Organometallics 2018, 37, 2832-2836;
D. Schmiel, H. Butenschön, Organometallics 2017, 36, 4979-4989;
W.-T. Zhao, Z.-Q. Lu, H. Zheng, X.-S. Xue, D. Zhao, ACS Catal. 2018, 8, 7997-8005;
Z.-Z. Zhang, G. Liao, H.-M. Chen, B.-F. Shi, Org. Lett. 2021, 23, 2626-2631;
K. Kanemoto, N. Horikawa, S. Hoshino, Y. Tokoro, S.-i. Fukuzawa, Org. Lett. 2021, 23, 4966-4970.
K. Plevová, B. Mudráková, E. Rakovský, R. Šebesta, J. Org. Chem. 2019, 84, 7312-7319.
J.-B. Xia, S.-L. You, Organometallics 2007, 26, 4869-4871.
M. Sattar, S. Kumar, Org. Lett. 2017, 19, 5960-5963.
D.-W. Gao, Q. Gu, S.-L. You, J. Am. Chem. Soc. 2016, 138, 2544-2547.
Z.-J. Cai, C.-X. Liu, Q. Gu, C. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2019, 58, 2149-2153;
Angew. Chem. 2019, 131, 2171-2175.
A. B. Charette, R. Chinchilla, C. Nájera, in Encyclopedia of Reagents for Organic Synthesis, 2007.
C. A. Salazar, J. J. Gair, K. N. Flesch, I. A. Guzei, J. C. Lewis, S. S. Stahl, Angew. Chem. Int. Ed. 2020, 59, 10873-10877;
Angew. Chem. 2020, 132, 10965-10969.
V. I. Sokolov, L. L. Troitskaya, O. A. Reutov, J. Organomet. Chem. 1977, 133, C28-C30.
R. J. Nielsen, W. A. Goddard, J. Am. Chem. Soc. 2006, 128, 9651-9660.
C. D. T. Nielsen, J. Burés, Chem. Sci. 2019, 10, 348-353;
J. Burés, Angew. Chem. Int. Ed. 2016, 55, 2028-2031;
Angew. Chem. 2016, 128, 2068-2071.
R. Peverati, D. G. Truhlar, J. Phys. Chem. Lett. 2012, 3, 117-124.
T. N. Truong, E. V. Stefanovich, Chem. Phys. Lett. 1995, 240, 253-260;
V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001.
J. Contreras-García, E. R. Johnson, S. Keinan, R. Chaudret, J.-P. Piquemal, D. N. Beratan, W. Yang, J. Chem. Theory Comput. 2011, 7, 625-632.
Z. Liang, J. Zhao, Y. Zhang, J. Org. Chem. 2010, 75, 170-177;
J. K. Laha, R. A. Bhimpuria, D. V. Prajapati, N. Dayal, S. Sharma, Chem. Commun. 2016, 52, 4329-4332.
S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012, 45, 936-946.