Stereoselective Synthesis of o-Bromo (or Iodo)aryl P-Chirogenic Phosphines Based on Aryne Chemistry

The efficient synthesis of chiral or achiral tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne specie...

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Veröffentlicht in:Journal of organic chemistry 2012-07, Vol.77 (13), p.5759-5769
Hauptverfasser: Bayardon, Jérôme, Laureano, Hugo, Diemer, Vincent, Dutartre, Mathieu, Das, Utpal, Rousselin, Yoann, Henry, Jean-Christophe, Colobert, Françoise, Leroux, Frédéric R, Jugé, Sylvain
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container_end_page 5769
container_issue 13
container_start_page 5759
container_title Journal of organic chemistry
container_volume 77
creator Bayardon, Jérôme
Laureano, Hugo
Diemer, Vincent
Dutartre, Mathieu
Das, Utpal
Rousselin, Yoann
Henry, Jean-Christophe
Colobert, Françoise
Leroux, Frédéric R
Jugé, Sylvain
description The efficient synthesis of chiral or achiral tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne species in the presence of n-butyllithium. When P-chirogenic secondary phosphine boranes were used, the corresponding o-halogeno-arylphosphine boranes were obtained without racemization in moderate to good yields and with ee up to 99%. The stereochemistry of the reaction, with complete retention of the configuration at the P atom, has been established by X-ray structures of P-chirogenic o-halogenophenyl phosphine borane complexes. The decomplexation of the borane was easily achieved without racemization using DABCO to obtain the free o-halogeno-arylphosphines in high yields.
doi_str_mv 10.1021/jo300910w
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Org. Chem</addtitle><description>The efficient synthesis of chiral or achiral tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne species in the presence of n-butyllithium. When P-chirogenic secondary phosphine boranes were used, the corresponding o-halogeno-arylphosphine boranes were obtained without racemization in moderate to good yields and with ee up to 99%. The stereochemistry of the reaction, with complete retention of the configuration at the P atom, has been established by X-ray structures of P-chirogenic o-halogenophenyl phosphine borane complexes. 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source American Chemical Society (ACS) Journals
subjects B derivatives
Chemical Sciences
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Preparations and properties
title Stereoselective Synthesis of o-Bromo (or Iodo)aryl P-Chirogenic Phosphines Based on Aryne Chemistry
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