Abstract
Benzofulvenes and their derivatives are useful molecular entities having applications as biologically active molecules, polymer precursors, and optoelectronic devices. We have developed a simple and mild synthetic method for the formulation of a variety of these interesting compounds. Using carbonyl coupling techniques combined with microwave heating, a wide variety of functionalized benzofulvenes can be accessed rapidly in good yield. Furthermore, we have obtained five crystal structures further expanding a limited number of benzofulvene structures available.
Highlights
Fulvene-based motifs are widely regarded as molecules of great interest,[1] arguably owing to their increasing presence in pharmaceutical applications,[2] molecular materials,[3] use as synthetic precursors,[4] and overall intriguing physical and chemical properties
To that end we have been engaged in modifying and optimizing a traditional route to the benzofulvene core[10] by utilizing substituted indanones to produce known and many novel functionalized benzofulvenes in three simple synthetic steps (Scheme 1)
We describe our work synthesizing a variety of functionalized benzofulvenes via a simple and mild method
Summary
Many preparations use metal catalysts that must be fully removed before any applied use of the fulvene.[6] Recently, there has been an effort to focus on cyclization reactions of enediynes,[7] alkynyl derivatives,[8] and transition-metal-based transformations[9] to obtain these valuable functionalized fulvenes. While these methods have greatly improved our abilities to access a wealth of benzofulvene-based motifs, there is arguably room in this mix for a simple and effective synthetic solution. To that end we have been engaged in modifying and optimizing a traditional route to the benzofulvene core[10] by utilizing substituted indanones to produce known and many novel functionalized benzofulvenes in three simple synthetic steps (Scheme 1)
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