2004
DOI: 10.1002/anie.200454084
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A LiCl‐Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl‐ and Heteroarylmagnesium Compounds from Organic Bromides

Abstract: Polyfunctionalized organometallic reagents are ubiquitous intermediates in modern organic chemistry.[1] One of the best methods for preparing these reagents is the halogen-metal exchange reaction. [1, 2] Whereas Br/Li exchange is fast and occurs at low temperatures, the corresponding Br/Mg exchange [3] is considerably slower, which limits its synthetic application for several reasons: 1) The exchange requires higher reaction temperatures and is therefore not compatible with many functional groups; 2) The slow… Show more

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Cited by 887 publications
(536 citation statements)
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“…The reaction proceeds by way of a modified Grignard greatly increased rates of formation of the Grignard intermediates [124].…”
Section: Scheme 63mentioning
confidence: 99%
“…The reaction proceeds by way of a modified Grignard greatly increased rates of formation of the Grignard intermediates [124].…”
Section: Scheme 63mentioning
confidence: 99%
“…183 This exchange reaction can also be performed using i-PrMgCl⋅LiCl, the lithium salt enhancing the reactivity of the created arylmagnesium by breaking the Grignard polymeric aggregates. 184 This procedure has been applied to some heteroaryl bromides such as 3-thienyl bromide, the resulting organomagnesium being used in an addition reaction to benzaldehyde. 184 Thiazolylmagnesiums metalated at C-2 have been obtained by the usual bromine-magnesium exchange using alkyl Grignards, even regioselectively, as it can be seen in Scheme 26 where the 2-thiazolylmagnesium bromide 86 is obtained from 2,4-dibromothiazole (85).…”
Section: Aromatic Five-membered Ringsmentioning
confidence: 99%
“…184 This procedure has been applied to some heteroaryl bromides such as 3-thienyl bromide, the resulting organomagnesium being used in an addition reaction to benzaldehyde. 184 Thiazolylmagnesiums metalated at C-2 have been obtained by the usual bromine-magnesium exchange using alkyl Grignards, even regioselectively, as it can be seen in Scheme 26 where the 2-thiazolylmagnesium bromide 86 is obtained from 2,4-dibromothiazole (85). This reagent has been used in an addition reaction to the chiral nitrile 87 affording, after reduction, the amine 88, a building block for the synthesis of thiazolyl peptides.…”
Section: Aromatic Five-membered Ringsmentioning
confidence: 99%
“…Thus, the TIPS group was removed to give the primary alcohol 49, which was oxidized to the aldehyde, and reacted with the aryl Grignard reagent 50 generated in situ using Knochel s technique. 31 Subsequent oxidation using the Dess Martin reagent gave the desired ketone 51 as the substrate for the intramolecular Heck reaction. The crucial Heck cyclization proceeded uneventfully with the aid of the ketone tether, to afford tetralone 52 in 96% yield.…”
mentioning
confidence: 99%