Synthesis of C6F5-substituted aminoethanols via acetate ion mediated C6F5-group transfer reaction

被引：15

作者：

Levin, VV

Dilman, AD

Belyakov, PA

Korlyukov, AA

Struchkova, MI

Antipin, MY

Tartakovsky, VA

机构：

[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia

[2] AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2006年 / 03期

关键词：

silicon; hypercoordination; amino alcohols; imines; tris(pentafluorophenyl)silyl derivatives;

D O I：

10.1055/s-2006-926278

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach for the synthesis of N-(pentafluorophenylmethyl)aminoethanols is developed. The method includes alkylation of imines with 2-tris(pentafluorophenyl)silyloxyethyl triflate, prepared from ethylene oxide and (C6F5)(3)SiOTf, to give 2-sityloxy-ethyliminium ions. Their treatment with sodium acetate induces CC bond formation proceeding as transfer of the C6F5 group from the five-coordinate silicate intermediate to the iminium center.

引用

页码：489 / 495

页数：7

共 50 条

[11] STUDY OF THE VIBRATIONAL DEACTIVATION IN C6F5H, C6F6, C6F5CL VAPORS
VASILENKO, LS
DYUBA, NM
PETROV, AK
RUBTSOVA, NN
OPTIKA I SPEKTROSKOPIYA, 1981, 51 (01): : 120 - 123
[12] Thermodynamic Characteristics of Silver Perfluorobenzoates C6F5COOAg·0.5C6F5COOH and C6F5COOAg
I. P. Malkerova
D. B. Kayumova
E. V. Belova
M. A. Shmelev
A. A. Sidorov
I. L. Eremenko
A. S. Alikhanyan
Russian Journal of Coordination Chemistry, 2022, 48 : 84 - 88
[13] Thermodynamic Characteristics of Silver Perfluorobenzoates C6F5COOAg•0.5C6F5 COOH and C6F5 COOAg
Malkerova, I. P.
Kayumova, D. B.
Belova, E. V.
Shmelev, M. A.
Sidorov, A. A.
Eremenko, I. L.
Alikhanyan, A. S.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2022, 48 (02) : 84 - 88
[14] RAYLEIGH SCATTERING OF LIGHT IN C5F6, C6F4CL2 AND C6F5CL
KVASOVA, LE
SUKHOTIN.GG
VESTNIK MOSKOVSKOGO UNIVERSITETA SERIYA 2 KHIMIYA, 1970, 11 (05): : 641 - &
[15] Electron attachment and detachment:: C6F5Cl, C6F5Br, and C6F5I and the electron affinity of C6F5Cl -: art. no. 012702
Miller, TM
Viggiano, AA
PHYSICAL REVIEW A, 2005, 71 (01):
[16] SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF THE PT2(II,III) COMPLEX (NBU4)[(C6F5)2PT(MU-C6F5)2PT(C6F5)2] AND THE PT2(III,III) COMPLEX (NBU4)[(C6F5)2PT(MU-C6F5CL)(MU-C6F5)PT(C6F5)2] - NOVEL LIGAND REACTIVITY OF A BRIDGING C6F5 GROUP
USON, R
FORNIES, J
TOMAS, M
CASAS, JM
COTTON, FA
FALVELLO, LR
FENG, XJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4145 - 4154
[17] FALP STUDIES OF ELECTRON-ATTACHMENT REACTIONS OF C6F5CL,C6F5BR AND C6F5I
HERD, CR
ADAMS, NG
SMITH, D
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 1989, 87 (03) : 331 - 342
[18] Accessing Highly Substituted Indoles via B(C6F5)3-Catalyzed Secondary Alkyl Group Transfer
Elsherbeni, Salma A.
Melen, Rebecca L.
Pulis, Alexander P.
Morrill, Louis C.
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (06): : 4244 - 4248
[19] B(C6F5)3- and HB(C6F5)2-mediated transformations of isothiocyanates
Fischer, Malte
Schmidtmann, Marc
CHEMICAL COMMUNICATIONS, 2020, 56 (46) : 6205 - 6208
[20] Reductive elimination of C6F5-C6F5 in the reaction of bis(pentafluorophenyl) palladium(II) complexes with protic acids
Koizumi, Take-aki
Yamazaki, Atsuko
Yamamoto, Takakazu
DALTON TRANSACTIONS, 2008, (30) : 3949 - 3952

← 1 2 3 4 5 →