237763-16-5Relevant articles and documents
Continuous Flow Preparation of (Hetero)benzylic Lithiums via Iodine-Lithium Exchange Reaction under Barbier Conditions
Weidmann, Niels,Harenberg, Johannes H.,Knochel, Paul
, p. 5895 - 5899 (2020/08/12)
Herein we report the generation of benzylic lithiums via an iodine-lithium exchange reaction on benzylic iodides performed in continuous flow using tBuLi as the exchange reagent. The resulting benzylic lithium species are trapped in situ by carbonyl electrophiles under Barbier conditions, resulting in benzylic secondary and tertiary alcohols. This flow procedure further allows the generation of highly reactive heterobenzylic lithium compounds, which are difficult to generate under batch conditions. A general scale-up was possible without further optimization.
Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: Applications in organic synthesis
Suh, YoungSung,Lee, Jun-Sik,Kim, Seoung-Hoi,Rieke, Reuben D.
, p. 20 - 36 (2007/10/03)
The use of highly active manganese (Mn)*, prepared by the Rieke method, was investigated for the direct preparation of benzylic manganese reagents. The oxidative addition of the highly active manganese to benzylic halides was easily completed under mild conditions. Moreover, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon-oxygen bonds of benzylic sulfonates and phosphates. The resulting benzylic manganese reagents were found to undergo cross-coupling reactions with a variety of electrophiles. Most of these reactions were carried out in the absence of any transition metal catalyst under mild conditions. In addition, the use of highly active manganese was also studied for preparation of homo-coupled products of functionalized benzyl halides without transition metal catalysts. These useful approaches provided not only a facile synthetic route to the preparation of resoricinolic lipids but a facile synthesis of functionalized 4-benzylpyridines by regioselective and chemo selective γ-addition of benzylic group to N-alkoxycarbonylpyridinum salts.
A new synthetic protocol for the direct preparation of organomanganese reagents; organomanganese tosylates and mesylates
Kim, Seung-Hoi,Rieke, Reuben D.
, p. 4931 - 4934 (2007/10/03)
A new synthetic route to organomanganese sulfonate reagents has been developed. These useful reagents can be readily prepared via direct oxidative addition of highly reactive manganese to carbon-oxygen bonds of the corresponding tosylates and mesylates under mild conditions.
