Preparation of tri- and difluoromethylated amines from aldimines using (trifluoromethyl) trimethylsilane

被引：57

作者：

Prakash, G. K. Surya ^{[1
]}

Mogi, Ryo

Olah, George A.

机构：

[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA

[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 16期

关键词：

D O I：

10.1021/ol061357w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of a trifluoromethyl group into aldimines was accomplished using ( trifluoromethyl) trimethylsilane with tetraalkylammonium fluorides as initiators, and the resulting adducts were converted to difluoromethylated imines in the presence of excess fluoride. The imines were reduced to difluoromethylated amines using sodium borohydride.

引用

页码：3589 / 3592

页数：4

共 33 条

[1] Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes
Amii, H
Kobayashi, T
Hatamoto, Y
Uneyama, K
[J]. CHEMICAL COMMUNICATIONS, 1999, (14) : 1323 - 1324
[2] New C-F bond-cleavage route for the synthesis of octafluoro[2.2]paracyclophane
Amii, H
Hatamoto, Y
Seo, M
Uneyama, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) : 7216 - 7218
[3] Extending the scope of Ruppert's reagent: trifluoromethylation of imines
Blazejewski, JC
Anselmi, E
Wilmshurst, MP
[J]. TETRAHEDRON LETTERS, 1999, 40 (30) : 5475 - 5478
[4] HYDROGEN-BOND DONOR PROPERTIES OF THE DIFLUOROMETHYL GROUP
ERICKSON, JA
MCLOUGHLIN, JI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) : 1626 - 1631
[5] STEREOSELECTIVE ADDITION OF CF(3)SIME(3) ON AZIRINES - SYNTHESIS OF (E)-AZIRIDINES
FELIX, CP
KHATIMI, N
LAURENT, AJ
[J]. TETRAHEDRON LETTERS, 1994, 35 (20) : 3303 - 3304
[6] The reduction of α-silyloxy ketones using phenyldimethylsilyllithium
Fleming, I
Roberts, RS
Smith, SC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (07): : 1215 - 1228
[7] HAGIWARA T, 1995, SYNLETT, P717
[8] A new sequential defluorination route to α-fluoro-α,β-unsaturated ketones from trifluoromethyl ketones
Hata, H
Kobayashi, T
Amii, H
Uneyama, K
Welch, JT
[J]. TETRAHEDRON LETTERS, 2002, 43 (35) : 6099 - 6102
[9] Kirsch P., 2013, MODERN FLUOROORGANIC
[10] A NOVEL DEHYDROFLUORINATION OF 2-(TRIFLUOROMETHYL)DIHYDRO-3,5-PYRIDINEDICARBOXYLATES TO 2-(DIFLUOROMETHYL)-3,5-PYRIDINEDICARBOXYLATES
LEE, LF
STIKES, GL
MOLYNEAUX, JM
SING, YL
CHUPP, JP
WOODARD, SS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2872 - 2877

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