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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Diarylmethanols Synthesis by Nickel(II)-catalyzed Addition of Arylboronic Acids to Aryl Aldehydes

Author(s): Fusheng Bie*, Xuejing Liu , Meng Wang, Haizhu Cui, Tang Li, Jie Ma and Han Cao*

Volume 17, Issue 4, 2020

Page: [248 - 253] Pages: 6

DOI: 10.2174/1570178616666190724124849

Price: $65

Abstract

A practical procedure for the addition of arylboronic acids to aromatic aldehydes has been developed in the presence of NiCl2(PPh3)2/1,3-bis-(2,6-diisopropylphenyl)imidazolium chloride (IPr·HCl) system with good yield. Generally, electron-rich and -neutral aryl aldehydes showed excellent reactivity and provided desired products in high yields. This procedure will provide new way to the synthesis of diarylmethanols.

Keywords: Arylboronic acids, aromatic aldehydes, diarylmethanols, nickel, addition, catalysis.

Graphical Abstract
[1]
Sankalan, M.; Gautam, P. RSC Advances, 2014, 4, 28317-28358.
[http://dx.doi.org/10.1039/C4RA01341G]
[2]
Weidmann, B.; Widler, L.; Olivero, A.G.; Maycock, C.D.; Seebach, D. Helv. Chim. Acta, 1981, 64, 357-361.
[http://dx.doi.org/10.1002/hlca.19810640136]
[3]
Pearce, P.J.; Richards, D.H.; Scilly, N.F. J. Chem. Soc. Perkin, 1972, 1:(1972-1999), 1655-1660.
[4]
Orizu, I.; Bolshan, Y. Tetrahedron Lett., 2016, 57, 5798-5800.
[http://dx.doi.org/10.1016/j.tetlet.2016.11.044]
[5]
Furuyama, T.; Yonehara, M.; Arimoto, S.; Kobayashi, M.; Matsumoto, Y.; Uchiyama, M. Chemistry, 2008, 14(33), 10348-10356.
[http://dx.doi.org/10.1002/chem.200800536] [PMID: 18816554]
[6]
Werner, T.; Bauer, M.; Riahi, A.M.; Schramm, H. Eur. J. Org. Chem., 2014, 4876-4883.
[http://dx.doi.org/10.1002/ejoc.201402138]
[7]
Masaaki, S.; Masato, U.; Norio, M. Angew. Chem. Int. Ed., 1998, 37, 3279-3281.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19981217)37:23<3279:AID-ANIE3279>3.0.CO;2-M]
[8]
Masato, U.; Norio, M. J. Org. Chem., 2000, 65, 4450-4452.
[http://dx.doi.org/10.1021/jo000187c] [PMID: 10891153]
[9]
Alexandre, F.T.; Pedro, M.P.G.; Luis, F.V.; Vania, A.; Teresa, M. J. Org. Chem., 2008, 73, 4076-4086.
[10]
James, W.; Gareth, P.; Pawel, P.; Christopher, F. Tetrahedron Lett., 2009, 50, 7365-7368.
[http://dx.doi.org/10.1016/j.tetlet.2009.10.082]
[11]
Chun, X.; Tao, L.; Jin, Z.; Jaclynn, E.; Qiao, H. Tetrahedron Lett., 2009, 50, 4953-4957.
[http://dx.doi.org/10.1016/j.tetlet.2009.06.074]
[12]
Alexandre, F.T.; Vania, A.M.T.D.; Luis, F.V.; Pedro, M.P.G.; Carlos, A.M.A. Tetrahedron, 2010, 66, 8494-8502.
[http://dx.doi.org/10.1016/j.tet.2010.08.050]
[13]
Serpil, D.; Hayati, T.; Bekir, C. Tetrahedron Lett., 2014, 55, 4129-4132.
[http://dx.doi.org/10.1016/j.tetlet.2014.05.125]
[14]
Jiefang, Y.; Xingyu, C.; Zhiqian, W. Tetrahedron Lett., 2015, 56, 5673-5675.
[http://dx.doi.org/10.1016/j.tetlet.2015.08.076]
[15]
Tetsuya, Y.; Tetsuo, O.; Yoshihiko, I. Org. Lett., 2005, 7, 4153-4155.
[http://dx.doi.org/10.1021/ol051501y] [PMID: 16146375]
[16]
Kiyoto, S.; Takafumi, A.; Satoru, I.; Yuka, M.; Kazuhiro, K.; Toyohiko, A. Tetrahedron Lett., 2006, 47, 5789-5792.
[http://dx.doi.org/10.1016/j.tetlet.2006.05.184]
[17]
Changming, Q.; Huayue, W.; Jiang, C.; Xian, C.; Miaochang, L.; Weiwei, Z. J. Org. Chem., 2007, 72, 4102-4107.
[18]
Ping, H.; Yong, L.; Chengguo, D.; Qiaosheng, H. Org. Lett., 2007, 9, 343-346.
[http://dx.doi.org/10.1021/ol062814b] [PMID: 17217300]
[19]
Ping, H.; Yong, L.; Qiao, H. Tetrahedron Lett., 2007, 48, 5283-5288.
[http://dx.doi.org/10.1016/j.tetlet.2007.05.119] [PMID: 18648490]
[20]
Masami, K.; Rumiko, S. J. Org. Chem., 2008, 73, 1597-1600.
[21]
Masami, K.; Rumiko, S.; Terumichi, E. J. Org. Chem., 2008, 73, 6939-6942.
[22]
Ajuan, Y.; Baoli, C.; Yangjie, W.; Jingya, L.; Kun, W. Tetrahedron Lett., 2008, 49, 5405-5407.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.003]
[23]
Masami, K.; Natsuki, I.; Rumiko, S.; Osamu, O. Tetrahedron, 2010, 66, 6814-6819.
[http://dx.doi.org/10.1016/j.tet.2010.06.049]
[24]
Tetsuya, Y.; Takuma, F.; Azamat, Z.; Tetsu, Y.; Yohei, O.; Tetsuo, O. Tetrahedron, 2015, 71, 19-26.
[http://dx.doi.org/10.1016/j.tet.2014.11.051]
[25]
Yuan, L.; Chun, X.; Ping, H.; Qiao, H. Org. Lett., 2008, 10, 2509-2512.
[http://dx.doi.org/10.1021/ol800774c] [PMID: 18465865]
[26]
Go, T.; Eiji, S.; Teruhisa, T.; Yusuke, K. Chem. Commun. (Camb.), 2005, 1459-1461.
[27]
Takafumi, A.; Kazuhiro, K.; Toyohiko, A. Tetrahedron Lett., 2007, 48, 4115-4117.
[http://dx.doi.org/10.1016/j.tetlet.2007.04.025]
[28]
Jean, B.; Kenichiro, I. Org. Lett., 2009, 11, 4410-4413.
[http://dx.doi.org/10.1021/ol9017613] [PMID: 19708680]
[29]
Li, Z.; Xin, D.; Ren, H.; Zhenhua, C.; Ming, B. Tetrahedron Lett., 2009, 50, 406-408.
[http://dx.doi.org/10.1016/j.tetlet.2008.11.018]
[30]
Chun, X.; Qiao, H. Tetrahedron Lett., 2010, 51, 924-927.
[http://dx.doi.org/10.1016/j.tetlet.2009.12.033]
[31]
Wen, C.; Mostafa, B.; Oliver, C. Tetrahedron Lett., 2011, 52, 1677-1679.
[32]
Jaganathan, K.; Masilamani, J. Chemistry, 2010, 16, 8989-8992.
[33]
Daisuke, T.; Motomu, K.; Masakatsu, S. Chem. Asian J., 2006, 1-2, 161-166.
[34]
Hanmei, Z.; Qiang, Z.; Jiuxi, C.; Miaochang, L.; Shuanghua, C.; Jinchang, D. J. Org. Chem., 2009, 74, 943-945.
[35]
Tao, Z.; Sha, P.; Jin, L. Org. Lett., 2009, 11, 453-456.
[http://dx.doi.org/10.1021/ol9008393] [PMID: 19128194]
[36]
Yasunori, Y.; Kazunori, K.; Norio, M. Angew. Chem. Int. Ed., 2009, 48, 4414-4416.
[http://dx.doi.org/10.1002/anie.200901395]
[37]
Ke, L.; Naifu, H.; Renshi, L.; Weicheng, Y.; Wenjun, T. J. Org. Chem., 2013, 78, 6350-6355.
[http://dx.doi.org/10.1021/jo400850m] [PMID: 23705850]
[38]
Yuanxi, L.; Jie, D.; Qiaosheng, H. Tetrahedron Lett., 2018, 59, 1548-1550.
[http://dx.doi.org/10.1016/j.tetlet.2018.02.071] [PMID: 30333670]

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