ol9b02639_si_001.pdf (6.87 MB)
Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides
journal contribution
posted on 2019-08-22, 21:14 authored by Ming-Hui Zhu, Cheng-Long Yu, Ya-Lan Feng, Muhammad Usman, Dayou Zhong, Xin Wang, Nasri Nesnas, Wen-Bo LiuAn
efficient strategy for N/O-(deutero)alkylation of indoles and
phenols with alkoxides/alcohols as the alkylation reagents is described.
The consecutive detosylation/alkylation transformations feature mild
reaction conditions, high ipso-selectivity, and good
functional group tolerance (>50 examples). A one-pot selective
N-alkylation
of unprotected indoles with alcohols and TsCl is also realized. The
application of this method is demonstrated by the introduction of
isotope-labeled (CD3 and 13CH3) groups
using the readily accessible labeled alcohols and the synthesis of
pharmaceuticals.