Hideki Yorimitsu group


Thursday, 19 May, 2022

Francesca Leonelli  is pleased to invite you to the Department seminar

Reductive Metalation of Unsaturated Compounds in the Presence of Electrophiles

Hideki Yorimitsu photo di Hideki Yorimitsu

Department of Chemistry, Kyoto University, Japan

Photographer: AHideki Yorimitsu


Reductions of alkynes and arenes by alkali metal are textbook reactions to afford protonated products, trans-alkenes and 1,4-cyclohexadienes, respectively, via carbanions. However, such reductive metalation of π bonds has scarcely been used for the purpose of non-protonative transformations because of the extreme instability of putative radical anion or dianion intermediates. I will talk about the generation of carbanions by reductive metalation of unsaturated compounds in the presence of reduction-resistant electrophiles. Trialkoxyboranes represent electrophiles that are compatible with reduction with alkali metal and can trap carbanions by means of the vacant p orbital. These boron electrophiles enable reductive diboration of unsaturated compounds such as alkenes, alkynes, and arenes. Reductive anti-dimagnesiation and - dialumination of alkynes using magnesium- and aluminium-based reduction-resistant electrophiles will be also discussed.

References: Org. Lett. 2019, 21, 4739; Org. Lett. 2020, 22, 2303; Org. Lett. 2021, 23, 4613; ChemRxiv 2022, 10.26434/chemrxiv-2022-h72gz

The seminar will be held in room B, floor  I building S. Cannizzaro CU014, Monday 23 May at 12.00 a.m.

It can be followed in person or remotely on the Google Meet platform (link foi-zwbi-czq).

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