Abstract
In this review, we describe a simple and general procedure to accomplish selective photochemical reaction sequences for two chromophores that are responsive to similar light frequencies. The essence of the method is based on the exploitation of differences in the molar absorptivity at certain wavelengths of the photosensitive groups, which is enhanced by utilizing light-absorbing auxiliary filter molecules, or “sunscreens”. Thus, the filter molecule hinders the reaction pathway of the least absorbing molecule or group, allowing for the selective reaction of the other. The method was applied to various photochemical reactions, from photolabile protecting group removal to catalytic photoinduced olefin metathesis in different wavelengths and using different sunscreen molecules. Additionally, the sunscreens were shown to be effective also when applied externally to the reaction mixture, avoiding any potential chemical interactions between sunscreen and substrates and circumventing the need to remove the light-filtering molecules from the reaction mixture, adding to the simplicity and generality of the method.
Highlights
The use of light to carry out organic transformations has resurged dramatically in recent years [1]
The development of continuous flow techniques for photochemistry has made the execution of large-scale light-induced processes possible, overcoming the light transmittance issues associated with large-scale photochemical reactions [13,14,15,16,17]
Notable works in this field were reported by Bochet et al [20,21], for example by harnessing kinetic isotope effects to achieve chromatic orthogonality between two types of 2-nitrobenzyl based photolabile protecting groups (PPGs) [22] and even demonstrating the chromatic orthogonal
Summary
The use of light to carry out organic transformations has resurged dramatically in recent years [1]. Several chromatic orthogonal systems where two photosensitive moieties may be reacted in a commutative fashion with different colors of light have been designed [19] Notable works in this field were reported by Bochet et al [20,21], for example by harnessing kinetic isotope effects to achieve chromatic orthogonality between two types of 2-nitrobenzyl based photolabile protecting groups (PPGs) [22] and even demonstrating the chromatic orthogonal. PPG removal to light-induced catalytic olefin metathesis reactions and demonstrated with several metathesis reactions and demonstrated with several wavelengths and different filter molecules.
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