- ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis
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(Equation Presented) ROMPgel-supported triphenylphosphine was synthesized in three steps (67%) from norbornadiene, 4-bromoiodobenzene, and chlorodiphenylphosphine. The supported reagent has a high loading (2.5 mmol/g) and favorable swelling properties in organic solvents. It has been utilized for the conversion of alcohols to halides, the reduction of ozonides, and the isomerization of α,β-acetylenic esters and in the Staudinger reaction. In general, filtration of the resin from the reaction mixtures and evaporation gave the corresponding products in high yield and purity.
- Arstad, Erik,Barrett, Anthony G. M.,Hopkins, Brian T.,Koebberling, Johannes
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- Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling
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A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.
- Longwitz, Lars,Jopp, Stefan,Werner, Thomas
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p. 7863 - 7870
(2019/06/27)
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- A mild, phosphine-free method for the conversion of alcohols into halides (Cl, Br, I) via the corresponding O-alkyl isoureas
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A novel procedure for the conversion of primary and secondary alcohols into the corresponding alkyl chlorides, bromides and iodides is described. The transformation is high-yielding in the case of chlorides and bromides, tolerates a range of functional groups, and does not rely on the use of phosphines.
- Li, Zhengning,Crosignani, Stefano,Linclau, Bruno
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p. 8143 - 8147
(2007/10/03)
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