A constellation of deuterium-labeled silanes as a simple mechanistic probe not requiring absolute configuration determination.

Angew Chem Int Ed Engl

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de.

Published: October 2015

AI Article Synopsis

  • - A new probe for studying how reactions happen at the silicon atom was developed using a special form of silolane labeled with deuterium.
  • - The process involves hydrogenating a compound called 2,5-dihydrosilole with deuterium, leading to a mix of stereoisomers that can be analyzed using (2)H NMR spectroscopy.
  • - This technique is quick, user-friendly, and helps overcome issues found in older methods, proving useful for observing various chemical reactions involving silicon bonding.

Article Abstract

A new stereochemical probe for mechanisms at the silicon atom that is based on a deuterium-labeled silolane is synthesized and evaluated. The key synthetic step involves the hydrogenation of a 2,5-dihydrosilole with deuterium gas, giving a complex mixture of isochronic stereoisotopologues. The overall stereochemical imbalance of this mixture is evident in its (2) H NMR spectrum, which provides a good qualitative measure of changes in the configuration at the silicon atom. The technique is rapid, easy to use, and overcomes limitations and biases of traditional methods. The utility of this new procedure is demonstrated by tracking the stereochemical course of several classical reactions as well as contemporary catalytic transformations involving bond formation at the silicon atom.

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http://dx.doi.org/10.1002/anie.201500750DOI Listing

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