Art

J-GLOBAL ID：201702268429205235   Reference number：17A0599940

CATALYTIC AROMATIC BORYLATION VIA IN SITU-GENERATED BORENIUM SPECIES

in situ生成したボレニウム種を経由する接触的芳香族ホウ素化

Author (6)： KITANI Fumiya (RIKEN Center for Sustainable Resource Sci., Saitama, JPN) ,  KITANI Fumiya (Tokyo Univ. Sci., Tokyo, JPN) ,  TAKITA Ryo (RIKEN Center for Sustainable Resource Sci., Saitama, JPN) ,  IMAHORI Tatsushi (Tokyo Univ. Sci., Tokyo, JPN) ,  UCHIYAMA Masanobu (RIKEN Center for Sustainable Resource Sci., Saitama, JPN) ,  UCHIYAMA Masanobu (Univ. Tokyo, Tokyo, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 95  Issue： 1  Page： 158-166  Publication year： Jan. 25, 2017 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,  catalytic reaction ,  Lewis base ,  catalytic activity ,  *boration ,  aromatic compound ,  *oxygen heterocyclic compound ,  *boron heterocyclic compound ,  regiospecific reaction ,  Lewis base catalysis ,  borylation ,  regioselective reaction ,  sulfur heterocyclic compound

JST classification (2)： Other 5-membered rings with two or more hetero atoms  (CF07085F) ,  Catalytic reactions in general  (CB06080F)

Substance index (13)： Catecholborane ,  1-(Triisopropylsilyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrrole ,  1-Pyrrolizino-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzene ,  1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]piperidine ,  1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborole-2-yl)-1H-indole ,  1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,2,3,4-tetrahydroquinoline ,  2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-5,10-dimethyl-5,10-dihydrophenazine ,  2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-5-methoxythiophene ,  N,N-Dimethylaniline ,  N,N-Dimethyl-3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline ,  N,N-Dimethyl-3-bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline ,  2-(4-Dimethylaminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ,  Tetrahydrothiophene

Reference (9)：

• D. Hall, 'Boronic Acids: Preparation, Applications in Organic Synthesis and Medicine,' Wiely-VCH, Weinheim, 2005.
• For a review, see: (a) W. K. Chow, O. Y. Yuen, P. Y. Choy, C. M. So, C. P. Lau, W. T. Wong, and F. Y. Kwong, RSC Adv., 2013, 3, 12518; See also: (b) T. Ishiyama, M. Murata, and N. Miyaura, J. Org. Chem., 1995, 60, 7508.
• (a) Y. Nagashima, R. Takita, K. Yoshida, K. Hirano, and M. Uchiyama, J. Am. Chem. Soc., 2013, 135, 18730; (b) E. Yamamoto, K. Izumi, Y. Horita, and H. Ito, J. Am. Chem. Soc., 2012, 134, 19997.
• For reviews, see: (a) I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, and J. F. Hartwig, Chem. Rev., 2010, 110, 890; (b) J. F. Hartwig, Acc. Chem. Res., 2012, 45, 864; See also: (c) J. Takagi, K. Takahashi, T. Ishiyama, and N. Miyaura, J. Am. Chem. Soc., 2002, 124, 390; (d) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, and J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 8001; For recent examples with a characteristic selectivity, see: (e) Y. Saito, Y. Segawa, and K. Itami, J. Am. Chem. Soc., 2015, 137, 5193; (f) K. Kuninobu, H. Ida, M. Nishi, and M. Kanai, Nat. Chem., 2015, 7, 712.
• T. S. De Vries, A. Prokofjevs, and E. Vedejs, Chem. Rev., 2012, 112 , 4246.

Terms in the title (2)： 芳香族 ,  ホウ素化