Abstract
The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversion. When excess of phenylboronic acid was used, a mixture of isomeric tri-, tetra- and pentaphenyl-substituted derivatives in the ∼10:70:20 ratio was obtained, along with minor amounts of hydrodechlorination products.
References
J. B. Hoke, G. A. Gramiccioni, E. N. Balko, Appl. Catal., B, 1992, 1, 285.
F. Murena, E. Schioppa, Appl. Catal., B, 2000, 27, 257.
Y. Ukisu, S. Iimura, R. Uchida, Chemosphere, 1996, 33, 1523.
S. Zinovyev, A. Perosa, S. Yufit, P. Tundo, J. Catal., 2002, 211, 347.
Polychloroaromatic Compounds, Ed. H. Suschitzky, Plenum, New York, 1974, 543 pp.
A. A. Vasil’ev, A. S. Burukin, S. G. Zlotin, Russ. Chem. Rev., 2007, 76, 885.
T. I. Gorbunova, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Rev., 2010, 79, 511.
A. S. Burukin, A. A. Vasil’ev, A. O. Chizhov, S. G. Zlotin, Russ. Chem. Bull., 2005, 54, 970.
A. S. Burukin, A. A. Vasil’ev, N. L. Merkulova, A. O. Chizhov, E. A. Mistryukov, S. G. Zlotin, Russ. Chem. Bull., 2007, 56, 1467.
A. S. Burukin, A. A. Vasil’ev, N. L. Merkulova, M. I. Struchkova, S. G. Zlotin, Russ. Chem. Bull., 2006, 55, 118.
J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 9550.
J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem., 2000, 65, 1158.
J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc., 2004, 126, 13028.
T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc., 2005, 127, 4685.
R. Martin, S. Buchwald, Acc. Chem. Res., 2008, 41, 1461.
S. Reimann, P. Ehlers, M. Sharif, A. Spannenberg, P. Langer, Tetrahedron, 2016, 72, 1083.
I. V. Kuchurov, A. A. Vasil’ev, S. G. Zlotin, Mendeleev Commun., 2010, 20, 140.
D.-H. Lee, M.-J. Jin, Org. Lett., 2011, 13, 252.
T. Tu, Zh. Sun, W. Fang, M. Xu, Yu. Zhou, Org. Lett., 2012, 14, 4250.
A. A. Vasil’ev, A. S. Burukin, G. M. Zhdankina, S. G. Zlotin, Mendeleev Commun., 2021, 31, 400.
H. Sajiki, A. Kume, K. Hattori, K. Hirota, Tetrahedron Lett., 2002, 43, 7247.
P. S. Gribanov, G. A. Chesnokov, P. B. Dzhevakov, N. Yu. Kirilenko, S. A. Rzhevskiy, A. A. Ageshina, M. A. Topchiy, M. V. Bermeshev, A. F. Asachenko, M. S. Nechaev, Mendeleev Commun., 2019, 29, 147.
S. B. Soliev, A. V. Astakhov, D. V. Pasyukov, V. M. Chernyshev, Russ. Chem. Bull., 2020, 69, 683.
N. A. Bumagin, Russ. Chem. Bull., 2021, 70, 1483.
E. V. Verbitskiy, E. M. Dinastiya, O. S. Eltsov, E. F. Zhilina, A. V. Schepochkin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Mendeleev Commun., 2020, 30, 142.
E. S. Matyugina, A. L. Khandazhinskaya, S. N. Kochetkov, K. L. Seley-Radtke, Mendeleev Commun., 2020, 30, 231.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 169–172, January, 2022.
This paper does not contain descriptions of studies on animals or humans.
The authors declare no competing interests.
Rights and permissions
About this article
Cite this article
Vasil’ev, A.A., Burukin, A.S., Zhdankina, G.M. et al. Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands. Russ Chem Bull 71, 169–172 (2022). https://doi.org/10.1007/s11172-022-3392-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-022-3392-7