标题:The selective activation of a C-F bond with an auxiliary strong Lewis acid: a method to change the activation preference of C-F and C-H bonds
作者:Wang, Lin; Sun, Hongjian; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter
作者机构:[Wang, Lin; Sun, Hongjian; Li, Xiaoyan] Shandong Univ, Minist Educ, Key Lab Special Funct Aggregated Mat, Sch Chem & Chem Engn, Shanda Nanlu 27, Jinan 更多
通讯作者:Li, Xiaoyan
通讯作者地址:[Li, XY]Shandong Univ, Minist Educ, Key Lab Special Funct Aggregated Mat, Sch Chem & Chem Engn, Shanda Nanlu 27, Jinan 250199, Peoples R China.
来源:DALTON TRANSACTIONS
出版年:2016
卷:45
期:45
页码:18133-18141
DOI:10.1039/c6dt03235d
摘要:The selective activation of the C-F bonds in substituted (2,6-difluorophenyl) phenylimines (2,6-F2H3C6-(CvNH)-n'-R-C6H4 (n' = 2, R = H (1); n' = 2, R = Me (2); n' = 4, R = tBu (3))) by Fe(PMe3)(4) with an auxiliary strong Lewis acid (LiBr, LiI, or ZnCl2) was explored. As a result, iron(II) halides ((H5C6-(CvNH)-2-FH3C6) FeX(PMe3)(3) (X = Br (8); Cl (9)) and (n-RH4C6-(CvNH)-2'-FH3C6) FeX(PMe3)(3) (n = 2, R = Me, X = Br (11); n = 4, R = tBu, X = I (12))) were obtained. Under similar reaction conditions, using LiBF4 instead of LiBr or ZnCl2, the reaction of (2,6-difluorophenyl) phenylimine with Fe(PMe3)(4) afforded an ionic complex [(2,6F(2)H(3)C(6)-(CvNH)-H4C6) Fe(PMe3)(4)](BF4) (10) via the activation of a C-H bond. The method of C-F bond activation with an auxiliary strong Lewis acid is appropriate for monofluoroarylmethanimines. Without the Lewis acid, iron(II) hydrides ((2-RH4C6-(CvNH)-2'-FH3C6) FeH(PMe3)(3) (R = H (13); Me (14))) were generated from the reactions of Fe(PMe3)(4) with the monofluoroarylmethanimines (2-FH4C6-(CvNH)-2'-RC6H4 (R = H (4); Me (5))); however, in the presence of ZnCl2 or LiBr, iron(II) halides ((2-RH4C6-(CvNH)-H4C6) FeX(PMe3)(3) (R = H, X = Cl (15); R = Me, X = Br (16))) could be obtained through the activation of a C-F bond. Furthermore, a C-F bond activation with good regioselectivity in (pentafluorophenyl) arylmethanimines (F5C6-(C=NH)-2,6-Y2C6H3 (Y = F (6); H (7))) could be realized in the presence of ZnCl2 to produce iron(II) chlorides ((2,6-Y2H3C6-(C=NH)-F4C6) FeCl(PMe3)(3) (Y = F (17); H (18))). This series of iron(II) halides could be used to catalyze the hydrosilylation reaction of aldehydes. Due to the stability of iron(II) halides to high temperature, the reaction mixture was allowed to be heated to 100 degrees C and the reaction could finish within 0.5 h.
收录类别:EI;SCOPUS;SCIE
WOS核心被引频次:4
Scopus被引频次:4
资源类型:期刊论文
原文链接:https://www.scopus.com/inward/record.uri?eid=2-s2.0-84995745286&doi=10.1039%2fC6DT03235D&partnerID=40&md5=013040488acc7eccabcd8f6822d4c3f3
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