Siladifluoromethylation and Deoxo-trifluoromethylation of PV-H Compounds with TMSCF3: Route to PV-CF2- Transfer Reagents and P-CF3 Compounds

被引：23

作者：

Krishnamurti, Vinayak ^{[1
,2
]}

Barrett, Colby ^{[1
,2
]}

Prakash, G. K. Surya ^{[1
,2
]}

机构：

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

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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

关键词：

ALPHA-SILYLDIFLUOROMETHYLPHOSPHONATES; NUCLEOPHILIC TRIFLUOROMETHYLATION; DIFLUOROMETHYLATION; FLUORINE; ANALOGS; ALDEHYDES; DIFLUORINATION; POTENT; ARYL;

D O I：

10.1021/acs.orglett.9b00381

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for siladifluoromethylation of dialkyl phosphonates and secondary phosphine oxides with TMSCF3 to produce nucleophilic P-V-CF2- transfer reagents is disclosed, with multigram scale reactions included. Condition-dependent divergent reactivity under the established conditions is demonstrated by the formation of trifluoromethylphosphines. Both one-pot transformations are operationally simple and employ inexpensive materials. Mechanistic investigations suggest the divergent reactivity originates from a common intermediate, with Li+ concentration directing the chemoselectivity.

引用

页码：1526 / 1529

页数：4

共 15 条

[1] Siladifluoromethylation and deoxo-trifluoromethylation of PV-H compounds with TMSCF3: Route to PV-CF2-transfer reagents and P-CF3 compounds
Krishnamurti, Vinayak
Barrett, Colby
Prakash, Surya
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
[2] A Metal-Free Route to CF3-Containing Oxindoles by PhI(OAc)2-Mediated Trifluoromethylation of N-Arylacrylamides with TMSCF3
Fu, Weijun
Xu, Fengjuan
Fu, Yuqin
Xu, Chen
Li, Shihui
Zou, Dapeng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (04) : 709 - 712
[3] ORANOTIN COMPOUNDS AS REAGENTS .2. NEW SYNTHESIS OF CF3E COMPOUNDS OF TIN (E=P,AS)
ANSARI, S
GROBE, J
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1975, 30 (7-8): : 531 - 534
[4] HALOMETHYL-METAL COMPOUNDS .45. ORGANOMERCURY CF3CCL TRANSFER REAGENTS - PHHGCCL2CF3 AND PHHGCCLBRCF3
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (15) : 3714 - &
[5] ORGANOTIN COMPOUNDS AS REAGENTS .1. SIMPLE METHOD FOR PREPARATION OF (CF3)2EH AND CF3EH2 (E = P, AS)
ANSARI, S
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ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1975, 30 (7-8): : 651 - 652
[6] Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide
Kino, Tatsuhito
Nagase, Yu
Ohtsuka, Yuhki
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Tokuhisa, Kenji
Yamakawa, Tetsu
JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (01) : 98 - 105
[7] REACTIVE E=C(P-P)PI-SYSTEMS .6. REACTIONS OF THE PHOSPHAALKENE F3CP=CF2 WITH H ACIDIC COMPOUNDS
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ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1986, 41 (02): : 149 - 161
[8] PERFLUORMETHYL ELEMENT LIGANDS .24. ORGANOTIN COMPOUNDS AS REAGENTS .3. CLEAVAGE REACTIONS OF THE ELEMENT-ELEMENT-BOND IN COMPOUNDS OF THE TYPE RNE-ERM(R=CH3CF3-E=P,AS,S,SE,TE-N,M=U,2)
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[9] Me2ESiMe3 (E = As, N, P) compounds -: Efficient reagents for replacement of the fluorine atom by Me2E group in the complex [(η6-1-F-3,5-Me2C6H3)(η5-C5EtMe4)Rh](CF3SO3)2
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Shteingarts, VD
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (04) : 583 - 585
[10] Me2ESiMe3 (E = As, N, P) Compounds—Efficient Reagents for Replacement of the Fluorine Atom by Me2E Group in the Complex [(η6-1-F-3,5-Me2C6H3)(η5-C5EtMe4)Rh](CF3SO3)2 >
L. I. Goryunov
J. Grobe
V. D. Shteingarts
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