Task-Dependent Coordination Levels of SmI2

Sandeepan Maity, Amey Nimkar, Shmaryahu Hoz

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Ligation plays a multifaceted role in the chemistry of SmI2. Depending on the ligand, two of its major effects are increasing the reduction potential of SmI2, and in the case of a ligand, which is also a proton donor, it may also enhance the reaction by protonation of the radical anion generated in the preceding step. It turns out that the number of ligand molecules that are needed to maximize the reduction potential of SmI2 is significantly smaller than the number of ligand molecules needed for a maximal enhancement of the protonation rate. In addition to the economical use of the ligand, this information can also be utilized as a diagnostic tool for the reaction mechanism in differentiating between single and multistep processes. The possible pitfalls in applying this diagnostic tool to PCET and cyclization reactions are discussed.

Original languageEnglish
Pages (from-to)1994-1998
Number of pages5
JournalJournal of Organic Chemistry
Volume84
Issue number4
DOIs
StatePublished - 15 Feb 2019

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

Funding

This research was supported by the Israel Science Foundation (grant no. 583/15). We are grateful to Prof. Flowers for allowing Dr. Maity to carry out the triflate experiments in his laboratory.

FundersFunder number
Israel Science Foundation583/15

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