TY - JOUR
T1 - Synthesis of 1,1′-diarylethanes and related systems by displacement of trichloroacetimidates with trimethylaluminum
AU - Mahajani, Nivedita S.
AU - Chisholm, John D.
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/4/6
Y1 - 2018/4/6
N2 - Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1′-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.
AB - Benzylic trichloroacetimidates are readily displaced by trimethylaluminum under Lewis acid promoted conditions to provide the corresponding methyl substitution product. This method is a convenient way to access 1,1′-diarylethanes and related systems, which play a significant role in medicinal chemistry, with a number of systems owing their biological activity to this functionality. Most benzylic substrates undergo ready displacement, with electron deficient systems being the exception. The use of an enantiopure imidate showed significant racemization, implicating the formation of a cationic intermediate.
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U2 - 10.1021/acs.joc.8b00027
DO - 10.1021/acs.joc.8b00027
M3 - Article
C2 - 29478311
AN - SCOPUS:85045116641
SN - 0022-3263
VL - 83
SP - 4131
EP - 4139
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -