Intramolecular Aminoboration of Unfunctionalized Olefins
Chun-Hua Yang
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorYu-Shi Zhang
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorWen-Wen Fan
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorDr. Gong-Qing Liu
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yue-Ming Li
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)Search for more papers by this authorChun-Hua Yang
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorYu-Shi Zhang
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorWen-Wen Fan
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorDr. Gong-Qing Liu
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yue-Ming Li
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China)
Stake Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071 (P.R. China)Search for more papers by this authorAbstract
A direct and catalyst-free method for the intramolecular aminoboration of unfunctionalized olefins is reported. In the presence of BCl3 (1 equiv) as the sole boron source, intramolecular aminoboration of sulfonamide derivatives of 4-penten-1-amines, 5-hexen-1-amines, and 2-allylanilines proceeded readily without the use of any catalyst. The boronic acids obtained after hydrolysis could be converted into the corresponding pinacol borates in a straightforward manner by treatment with pinacol under anhydrous conditions.
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References
- 1
- 1aN. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457–2483;
- 1bA. J. J. Lennox, G. C. Lloyd-Jones, Chem. Soc. Rev. 2014, 43, 412–443;
- 1cS. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. Int. Ed. 2001, 40, 4544–4568;
10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N CAS PubMed Web of Science® Google ScholarAngew. Chem. 2001, 113, 4676–4701;
- 1dH. Doucet, Eur. J. Org. Chem. 2008, 2013–2030;
- 1eA. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722–6737; Angew. Chem. 2011, 123, 6854–6869.
- 2J. Adams, M. Kauffman, Cancer Invest. 2004, 22, 304–311.
- 3A. S. Gorovoy, O. V. Gozhina, J. S. Svendsen, A. A. Domorad, G. V. Tetz, V. V. Tetz, T. Lejon, Chem. Biol. Drug Des. 2013, 81, 408–413.
- 4
- 4aH. C. Brown, T. E. Cole, Organometallics 1983, 2, 1316–1319;
- 4bT. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508–7510.
- 5
- 5aH. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1971, 93, 1816–1818;
- 5bH. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1972, 94, 4370–4371;
- 5cH. C. Brown, N. G. Bhat, V. Somayaji, Organometallics 1983, 2, 1311–1316;
- 5dI. D. Gridnev, N. Miyaura, A. Suzuki, Organometallics 1993, 12, 589–592;
- 5eH. Yoshida, I. Kageyuki, K. Takaki, Org. Lett. 2014, 16, 3512–3515.
- 6
- 6aY. Satoh, H. Serizawa, N. Miyaura, S. Hara, A. Suzuki, Tetrahedron Lett. 1988, 29, 1811–1814;
- 6bC. Mazal, M. Vaultier, Tetrahedron Lett. 1994, 35, 3089–3090;
- 6cE. Chong, S. A. Blum, J. Am. Chem. Soc. 2015, 137, 10144–10147.
- 7
- 7aM. A. Beenen, C. An, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 6910–6911;
- 7bN. Hu, G. Zhao, Y. Zhang, X. Liu, G. Li, W. Tang, J. Am. Chem. Soc. 2015, 137, 6746–6749.
- 8
- 8aM. A. Larsen, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 4287–4299;
- 8bT. C. Atack, R. M. Lecker, S. P. Cook, J. Am. Chem. Soc. 2014, 136, 9521–9523.
- 9
- 9aD. S. Matteson, R. J. Moody, J. Org. Chem. 1980, 45, 1091–1095;
- 9bT. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 11018–11019.
- 10
- 10aN. Matsuda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2013, 135, 4934–4937;
- 10bR. Sakae, N. Matsuda, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2014, 16, 1228–1231;
- 10cR. Sakae, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2015, 54, 613–617; Angew. Chem. 2015, 127, 623–627;
- 10dR. Sakae, K. Hirano, M. Miura, J. Am. Chem. Soc. 2015, 137, 6460–6463.
- 11A. Parra, L. Amenós, M. Guisán-Ceinos, A. López, J. L. García Ruano, M. Tortosa, J. Am. Chem. Soc. 2014, 136, 15833–15836.
- 12G.-Q. Liu, Y.-M. Li, J. Org. Chem. 2014, 79, 10094–10109.
- 13C.-H. Yang, W.-W. Fan, G.-Q. Liu, L. Duan, L. Li, Y.-M. Li, RSC Adv. 2015, 5, 61081–61093.
- 14
- 14aB. M. Partridge, L. Chausset-Boissarie, M. Burns, A. P. Pulis, V. K. Aggarwal, Angew. Chem. Int. Ed. 2012, 51, 11795–11799; Angew. Chem. 2012, 124, 11965–11969;
- 14bA. P. Pulis, D. J. Blair, E. Torres, V. K. Aggarwal, J. Am. Chem. Soc. 2013, 135, 16054–16057.
- 15
- 15aP. G. Sammes, D. J. Weller, Synthesis 1995, 1205–1222;
- 15bJ. Kaneti, A. J. Kirby, A. H. Koedjikov, I. G. Pojarlieff, Org. Biomol. Chem. 2004, 2, 1098–1103;
- 15cM. E. Jung, G. Piizzi, Chem. Rev. 2005, 105, 1735–1766;
- 15dM. R. Crimmin, M. Arrowsmith, A. G. M. Barrett, I. J. Casely, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc. 2009, 131, 9670–9685;
- 15eN. T. Patil, V. S. Raut, R. D. Kavthe, V. V. N. Reddy, P. V. K. Raju, Tetrahedron Lett. 2009, 50, 6576–6579;
- 15fJ. Kostal, W. L. Jorgensen, J. Am. Chem. Soc. 2010, 132, 8766–8773;
- 15gC. Duncan, A. V. Biradar, T. Asefa, ACS Catal. 2011, 1, 736–750.
- 16Please refer to the Supporting Information for details.
- 17
- 17aG. Illuminati, L. Mandolini, Acc. Chem. Res. 1981, 14, 95–102;
- 17bA. J. Kirby in Advances in Physical Organic Chemistry, Vol. 17 (Eds.: ), Academic Press, London, New York, Toronto, Sydney, San Francisco, 1981, pp. 183–278;
- 17cT. G. Denisova, E. T. Denisov, Russ. Chem. Bull. 2002, 51, 949–960;
- 17dJ.-S. Ryu, T. J. Marks, F. E. McDonald, J. Org. Chem. 2004, 69, 1038–1052;
- 17eA. Dzudza, T. J. Marks, Chem. Eur. J. 2010, 16, 3403–3422.
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