Non-planar Boron Lewis Acids Taking the Next Step: Development of Tunable Lewis Acids, Lewis Superacids and Bifunctional Catalysts

This paper is dedicated to Prof. Paul Knochel with respect and admiration

Abstract

Although boron Lewis acids commonly adopt a trigonal planar geometry, a number of compounds in which the trivalent boron atom is located in a pyramidal environment have been described. This review will highlight the recent developments of the chemistry and applications of non-planar boron Lewis acids, including a series of non-planar triarylboranes derived from the triptycene core. A thorough analysis of the properties and of the influence of the pyramidalization of boron Lewis acids on their stereoelectronic properties and reactivities is presented based on recent theoretical and experimental studies.

1 Non-planar Trialkylboranes

2 Non-planar Alkyl and Aryl-Boronates

3 Non-planar Triarylboranes and Alkenylboranes

3.1 Previous Investigations on Bora Barrelenes and Triptycenes

3.2 Recent Work on Boratriptycenes from Our Research Group

4 Applications of Non-planar Boranes

4.1 Non-planar Alkyl Boranes and Boronates

4.2 Non-planar Triarylboranes (Boratriptycenes)

5 Other Non-planar Group 13 Lewis Acids

6 Further Work and Perspectives

Key words

boron Lewis acids - structural constraint - Lewis superacids - triarylboranes - boratriptycenes

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