Abstract
Naphthalene is certainly not a common arene. In contrast to benzene, the bicyclic
feature of naphthalene offers multiple differentiable positions and thus a broad diversity
of substitution patterns. Naphthalene is a central building block for the construction
of elaborated polycyclic architectures with applications in broad domains such as
life and materials sciences. As a result, C–H functionalization strategies specially
designed for naphthalene substrates have become essential to install valuable substituents
on one or both rings towards polysubstituted naphthalenes. This short review provides
a focus on uncommon substitution patterns; however, classical ortho C–H activation
is not covered.
1 Introduction
2 C–H Functionalization Using a Directing Group Located at Position 1
2.1 Functionalization on the Ring Bearing the DG: 1,3-Substitution Pattern
2.2 Functionalization on the Ring Bearing the DG: 1,4-Substitution Pattern
2.3 Functionalization on the Neighboring Ring: 1,6-, 1,7- and 1,8-Substitution Patterns
3 C–H Functionalization Using a Directing Group Located at Position 2
3.1 Functionalization on the Ring Bearing the DG: 2,4- and 2,1-Substitution Patterns
3.2 Miscellaneous Substitution Patterns
4 Bis C–H Functionalization
4.1 Symmetrical Bisfunctionalization: 1,2,8-Substitution Pattern
4.2 Symmetrical Bisfunctionalization: 2,3,1-Substitution Pattern
4.2 Unsymmetrical Bisfunctionalization: 2,3,1-Substitution Pattern
4.3 Symmetrical Bisfunctionalization: 2,4,8-Substitution Pattern
5 Conclusion and Outlook
Key words
naphthalene - C–H functionalization - directing groups - selectivity - catalysis
