Transhalogenation

The transhalogenation (also: halide metathesis ) is a reaction in which a halogen atom is exchanged for a halogen compound with another halogen atom, for example, the reaction of an alkyl chloride to an alkyl fluoride by sodium fluoride :

R-Cl + NaF → RF + NaCl

If the halogen compound is an organic compound, it is called the Finkelstein reaction . However, it is also possible, for example, to produce phosphorus fluoride compounds by means of transhalogenation of chlorine, bromine or iodine bound to phosphorus with a metal fluoride.

Details

Metal halides (such as sodium fluoride or lithium fluoride ) are often used as the halogen source for transhalogenation , but the use of onium halides is also possible. Transhalogenation has been described as a gentle method for the synthesis of fluororganylboranes. The production of aryl iodides from the corresponding aryl chlorides or aryl bromides is also possible.

An investigation showed a possibility to carry out the transhalogenation by means of genetically modified enzymes (haloalkane dehalogenases, HLDs).

literature

Yoel Sasson: Formation of Carbon-Halogen Bonds (Cl, Br, I) . In: PATAI'S Chemistry of Functional Groups . John Wiley & Sons, Ltd, Chichester, UK 2009, ISBN 978-0-470-68253-1 , pp. pat0011 , doi : 10.1002 / 9780470682531.pat0011 .
transhalogenation - Wiktionary. Retrieved February 23, 2020 .

Individual evidence

^ ^A ^b Yoel Sasson: Formation of Carbon-Halogen Bonds (Cl, Br, I) . In: PATAI'S Chemistry of Functional Groups . John Wiley & Sons, Ltd, Chichester, UK 2009, ISBN 978-0-470-68253-1 , pp. pat0011 , doi : 10.1002 / 9780470682531.pat0011 .
↑ Patent DE68918542T : Process for the transhalogenation of a halophosphorus compound with hydrogen fluoride. Published August 30, 1989 . ‌
↑ Gerd Bir, Wolfgang Schacht, Dieter Kaufmann: A general, simple and gentle synthesis method for fluororganylboranes . In: Journal of Organometallic Chemistry . tape 340 , no. 3 , February 23, 1988, ISSN 0022-328X , p. 267-271 , doi : 10.1016 / 0022-328X (88) 80020-2 .
↑ Alex C. Bissember, Martin G. Banwell: Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles † . In: The Journal of Organic Chemistry . tape 74 , no. 13 , July 3, 2009, ISSN 0022-3263 , p. 4893-4895 , doi : 10.1021 / jo9008386 .
↑ Andy Beier, Jiri Damborsky, Zbynek Prokop: Transhalogenation Catalysed by Haloalkane Dehalogenases Engineered to Stop Natural Pathway at Intermediate . In: Advanced Synthesis & Catalysis . April 17, 2019, ISSN 1615-4150 , p. adsc.201900132 , doi : 10.1002 / adsc.201900132 .

[Sasson-1] A ^b Yoel Sasson: Formation of Carbon-Halogen Bonds (Cl, Br, I) . In: PATAI'S Chemistry of Functional Groups . John Wiley & Sons, Ltd, Chichester, UK 2009, ISBN 978-0-470-68253-1 , pp. pat0011 , doi : 10.1002 / 9780470682531.pat0011 .

[2] Patent DE68918542T : Process for the transhalogenation of a halophosphorus compound with hydrogen fluoride. Published August 30, 1989 . ‌

[3] Gerd Bir, Wolfgang Schacht, Dieter Kaufmann: A general, simple and gentle synthesis method for fluororganylboranes . In: Journal of Organometallic Chemistry . tape 340 , no. 3 , February 23, 1988, ISSN 0022-328X , p. 267-271 , doi : 10.1016 / 0022-328X (88) 80020-2 .

[4] Alex C. Bissember, Martin G. Banwell: Microwave-Assisted Trans-Halogenation Reactions of Various Chloro-, Bromo-, Trifluoromethanesulfonyloxy- and Nonafluorobutanesulfonyloxy-Substituted Quinolines, Isoquinolines, and Pyridines Leading to the Corresponding Iodinated Heterocycles † . In: The Journal of Organic Chemistry . tape 74 , no. 13 , July 3, 2009, ISSN 0022-3263 , p. 4893-4895 , doi : 10.1021 / jo9008386 .

[5] Andy Beier, Jiri Damborsky, Zbynek Prokop: Transhalogenation Catalysed by Haloalkane Dehalogenases Engineered to Stop Natural Pathway at Intermediate . In: Advanced Synthesis & Catalysis . April 17, 2019, ISSN 1615-4150 , p. adsc.201900132 , doi : 10.1002 / adsc.201900132 .