53774-32-6Relevant academic research and scientific papers
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.
A practical method to stereospecifically synthesize trans-stilbene derivatives
Jian, Yujuan,Sun, Gaojun,Li, Jiaming,Su, Dan,Li, Chuanrun,Zhong, Guochen
, p. 1423 - 1428 (2011/10/31)
A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane (BTMS), which was driven by tetrabutylammonium fluoride (TBAF) in THF. At the same time a plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. Also this method was employed to synthesize three precursors of natural products with excellent yields, which demonstrated that this method is much efficient and practical in the synthesis of some natural products. A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane, which was driven by tetrabutylammonium fluoride in THF. A plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. This method was employed to synthesize three precursors of natural products with excellent yields. Copyright
Preparation of functionalized organomanganese(II) reagents by direct insertion of manganese to aromatic and benzylic halides
Peng, Zhihua,Knochel, Paul
supporting information; experimental part, p. 3198 - 3201 (2011/08/06)
Functionalized arylmanganese compounds were prepared using commercial manganese powder in the presence of LiCl and catalytic amounts of both 2.5% InCl3 and 2.5% PbCl2 (THF, 0-50 °C). In addition, benzylic manganese reagents are obtained at 25 °C in ca. 70-80% yield (in the absence of LiCl) using commercial manganese powder and catalytic amounts of 2.5% InCl3 and 2.5% PbCl2. The resulting organomanganese reagents undergo smooth 1,2-addition, acylation, allylic substitution, Pd-catalyzed cross-coupling, and copper-catalyzed conjugate addition, affording the desired products in good yields.
NOVEL SYNTHESIS OF BENZYLLITHIUMS FROM BENZYLSELENIDES
Clarembeau, M.,Krief, A.
, p. 1093 - 1096 (2007/10/02)
Benzylselenides are found to be valuable precursors of benzyllithiums.The scope of the new method is disclosed.
