ol6b01970_si_001.pdf (1.51 MB)
Collective Synthesis of 3‑Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3‑(Methylsulfonyl)indoles from Free (N–H) Indoles via Common N‑Indolyl Triethylborate
journal contribution
posted on 2016-07-25, 23:49 authored by Zhi-Wei Zhang, Hong Xue, Hailing Li, Huaiping Kang, Juan Feng, Aijun Lin, Shouxin LiuA general
and direct C3 functionalization of free (N–H)
indoles with readily available electrophiles such as acid chlorides,
chloroformates, thionyl chloride, and methylsulfonyl chloride via
a common N-indolyl triethylborate intermediate is
reported. The reaction proceeds smoothly under mild conditions in
up to 93% yield. Indoles with substituents at the C2, C4, C5, C6,
and C7 positions are well tolerated. The easy accessibility of a variety
of important 3-acylindoles, indole-3-carboxylic esters, indole-3-sulfinic
acids, and 3-(methylsulfonyl)indoles demonstrates the high degree
of compatibility and practicability of this method.