Melding of Experiment and Theory Illuminates Mechanisms of Metal-Catalyzed Rearrangements: Computational Approaches and Caveats

Dedicated to the memory of Prof. Marilyn Olmstead, a world-class leader in crystallography and extraordinary teacher and mentor

Abstract

This review summarizes approaches and caveats in computational modeling of transition-metal-catalyzed sigmatropic rearrangements involving carbene transfer. We highlight contemporary examples of combined synthetic and theoretical investigations that showcase the synergy achievable by integrating experiment and theory.

1 Introduction

2 Mechanistic Models

3 Theoretical Approaches and Caveats

3.1 Recommended Computational Tools

3.2 Choice of Functional and Basis Set

3.3 Conformations and Ligand-Binding Modes

3.4 Solvation

4 Synergy of Experiment and Theory – Case Studies

4.1 Metal-Bound or Free Ylides?

4.2 Conformations and Ligand-Binding Modes of Paddlewheel Complexes

4.3 No Metal, Just Light

4.4 How To ‘Cope’ with Nonstatistical Dynamic Effects

5 Outlook

Key words

rearrangements - rhodium catalysis - carbene transfer - onium­ ylides - DFT calculations

Publication History

Received: 28 April 2021

Accepted after revision: 26 May 2021

Article published online:
14 July 2021

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