Abstract

Ball mills input energy to samples by pulverising the contents of the jar. Each impact on the sample or wall of the jar results in an instantaneous transmission of energy in the form of a temperature and pressure increase (volume reduction). Conversely, enantioselective organocatalytic reactions proceed through perceived delicate and well‐organised transition states. Does there exist a dichotomy in the idea of enantioselective mechanochemical organocatalysis? This Review provides a survey of the literature reporting the combination of organocatalytic reactions with mechanochemical ball milling conditions. Where possible, direct comparisons of stirred in solution, stirred neat and ball milled processes are drawn with a particular focus on control of stereoselectivity.

Highlights

  • Mechanochemical processes use the input of mechanical force to affect a reaction

  • This study appears to mark the first example where ball-milling leads to improved enantioselectivity in an organocatalyzed reaction and features the use of water as a liquid assisted grinding (LAG) agent.[26]

  • While most of the ball-milling enabled organocatalysis has focused on secondary amine or hydrogen-bonding catalysts, there are a few reports that do not fit these descriptors

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Summary

Introduction

This publication is part of a joint Special Collection of Chemistry Methods and ChemSusChem including invited contributions focusing on “Methods and Applications in Mechanochemistry”. Www.chemsuschem.org absence of solvent, and the reactor environment of a ball mill is receiving increasing interest in recent times.[32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60]. The corresponding parameters for each reactor type are listed, including solvent, reaction time, catalyst loading, reaction temperature, stirring speed (where given) and, for ball milling, the type of mill, milling frequency and note of any liquid assisted grinding (LAG) agents[26,34,80] or grinding auxiliaries (GA)

Aldol reactions under ball-milling conditions
Other secondary amine-catalysed transformations under ball-milling conditions
Michael additions under ball-milling conditions
Hydrogen-bonding-mediated additions under ball-milling conditions
Morita-Baylis-Hillman reaction under ball-milling conditions
Acyl Anion Reactions Under Ball-Milling Conditions
Other Transformations Under Ball-Milling Conditions
Conclusions and Reflections
Findings
Conflict of Interest
Full Text
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