10.1021/acs.orglett.6b01970.s001
Zhi-Wei Zhang
Zhi-Wei
Zhang
Hong Xue
Hong
Xue
Hailing Li
Hailing
Li
Huaiping Kang
Huaiping
Kang
Juan Feng
Juan
Feng
Aijun Lin
Aijun
Lin
Shouxin Liu
Shouxin
Liu
Collective Synthesis of 3‑Acylindoles, Indole-3-carboxylic
Esters, Indole-3-sulfinic Acids, and 3‑(Methylsulfonyl)indoles
from Free (N–H) Indoles via
Common <i>N</i>‑Indolyl Triethylborate
American Chemical Society
2016
Indole
C 3 functionalization
acid chlorides
indole
Collective Synthesis
indolyl triethylborate
reaction proceeds
C 7 positions
thionyl chloride
methylsulfonyl chloride
2016-07-25 23:49:23
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Collective_Synthesis_of_3_Acylindoles_Indole-3-carboxylic_Esters_Indole-3-sulfinic_Acids_and_3_Methylsulfonyl_indoles_from_Free_N_H_Indoles_via_Common_i_N_i_Indolyl_Triethylborate/3498566
A 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 <i>N</i>-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.