• Enantiospecific Elongation of Cationic Helicenes by Electrophilic Functionalization at Terminal Ends
    Romain Duwald, Simon Pascal, Johann Bosson, Stephane Grass, Celine Besnard, Thomas Buergi and Jerome Lacour
    Chemistry - A European Journal, 23 (55) , 2017, p13596-13601
    Keywords: carbenium ions; helicenes; regioselectivity; SEAr; SNAr; thermodynamic control
    DOI:10.1002/chem.201703441 | unige:97330 | Abstract | Article HTML | Article PDF | Supporting Info
 
A strategy for late-stage electrophilic functionalizations of cationic helicenes is exposed. Thanks to strongly acidic conditions that permit reversible electrophilic substitutions, regioselective acylations, sulfonylations or alkylations occur at the extremity(ies) of the helical cores. Extended [5] or [6]helicenes can then be generated from cationic [4]helicenes in successive one-pot elongation processes. Retention of configuration and excellent enantiospecificity (up to 99%) are observed for the helicene growth in the enantiopure series.

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Besnard, Celine Bosson, Johann Buergi, Thomas Duwald, Romain Grass, Stephane 
Lacour, Jerome Pascal, Simon 
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