HIDEKI YORIMITSU'S SEMINARY
Francesca Leonelli is pleased to invite you to the Department seminar
Reductive Metalation of Unsaturated Compounds in the Presence of Electrophiles
di Hideki Yorimitsu
Department of Chemistry, Kyoto University, Japan
Abstract
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).