- Cs2CO3-promoted vinylation of phenols with trichloroethylene: Facile synthesis of (E)-1,2-dichloro-1-phenoxyethenes
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An efficient method for the synthesis of (E)-1,2-dichloro-1-phenoxyethenes 2 has been developed. The reaction of phenol derivatives 1 with trichloroethylene at ambient temperature by means of Cs2CO3-DMSO system furnished the correspo
- Takahashi, Kazunori,Mamiya, Naho,Fukushima, Kei,Tsubuki, Masayoshi,Honda, Toshio
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p. 1622 - 1630
(2018/10/04)
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- 2-substituted benzo[b]furans from (E)-1,2-dichlorovinyl ethers and organoboron reagents: Scope and mechanistic investigations into the one-pot Suzuki coupling/direct arylation
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2-Substituted benzo[b]furans can easily be assembled from simple phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid synthesis of many analogues using essentially the same chemistry, of particular value in drug development. Results of kinetic isotope effect studies and investigations into the regioselectivity of the process indicate that the direct arylation step most likely does not involve an electrophilic palladation. The most likely mechanism lies somewhere on the continuum between a C-H bond metathesis and an assisted palladation or concerted metallation-deprotonation pathway. A very efficient modular approach to the construction of benzo[b]furans using trichloroethylene as a scaffold is described. This method gives easy access to highlysubstituted heterocycles in only two synthetic operations, and is especially suitable for rapid construction of compound libraries.
- Geary, Laina M.,Hultin, Philip G.
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supporting information; experimental part
p. 5563 - 5573
(2010/12/29)
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- APPLICATION OF TRICHLOROETHYLENE IN ORGANIC SYNTHESIS. PART III. SYNTHESIS OF DICHLOROVINYL AROMATIC ETHERS
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A simple preparative method of synthesis of aromatic dichlorovinyl ethers was elaborated.The method is based on the reactions of phenols with trichloroethylene under phase-transfer conditions, in the presence of catalytic quantities of quaternary ammonium
- Pielichowski, Jan,Bogdal, Dariusz
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p. 483 - 487
(2007/10/02)
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- Urea derivatives and their use as herbicides
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Compounds, useful as herbicides, of the formula SPC1 Wherein R1 is haloalkyl, halocycloalkyl, haloalkenyl, or halocycloalkenyl; n1 is 1 or 2; R4 is halogen, trifluoromethyl, alkyl, or alkoxy; n2 is 0, 1, 2, or 3; R2 is hydrogen or alkyl; and R3 is alkyl or alkoxy. Methods for making these compounds.
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