Re-enter the syn-(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

Abstract

syn-α-Diiodobimane (syn-(R2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn-(R2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.

Highly tunable bimane-based fluorescent probes: design, synthesis, and application as a selective amyloid binding dye

“…22 In addition, bimane has the capability to act as an O-donor ligand in metal-bimane complexes, including those with Pd(II), Na(I), and Li(I). 23 However, with the exception of a few derivatives, [23][24][25] exploration of bimanes in complex biological applications has been limited due to their UV absorption and blue uorescence.…”

Shining light on fluoride detection: a comprehensive study exploring the potential of coumarin precursors as selective turn-on fluorescent chemosensors

“…17 While a significant fraction of this work used bimane fluorophores as the transducing (i.e., signaling) element, the requirement for de novo synthesis and feature optimization of these novel bimanes limited the practical utility of these methods. 18 In contrast to bimane fluorophores, many coumarin fluorophores are commercially available or readily accessible in only a few synthetic steps. Coumarin-based fluorescent chemosensors, therefore, have been used extensively in the detection of a variety of high-impact analytes, 19 including zinc(II), 20 copper(II), 21 and aluminum(III) cations, 22 as well as in the detection of fluoride anions.…”