TY - JOUR
TI - On the mechanism of the Au(I)-mediated addition of alkynes to anthranils to furnish 7-acylindoles
AU - Stylianakis, I.
AU - Litinas, I.
AU - Nieto Faza, O.
AU - Kolocouris, A.
AU - Silva López, C.
JO - Journal of Physical Organic Chemistry
PY - 2022
VL - null
TODO - null
SP - null
PB - John Wiley and Sons Ltd
SN - 0894-3230, 1099-1395
TODO - 10.1002/poc.4333
TODO - Gold compounds;  Hydrocarbons;  Organic solvents;  Reaction intermediates, Alkynyl activation;  Alkynyls;  Anthralin;  Gold catalysis;  Gold-carbenes;  Pharma industry;  Physical organic chemistry;  Reaction pathways;  Structural motifs;  Α-imino gold carbene, Regioselectivity
TODO - Indole is a very common structural motif in alkaloids with a remarkable history in pharma industry. In the continuous search for more direct and efficient access to these valuable structures, a new and rather elegant approach was found by Jin and coworkers, which involved a gold(I)-mediated addition of alkynes onto anthralins. This approach selectively furnishes 7-acylindoles in a rather expeditious way, and it has been shown to be compatible with a large range of decorated reactants, both at the alkyne side and at the anthralin side. We studied the mechanism of this reaction with a set of different alkynes, including disubstituted ones, to establish similarities and differences between them and to aid in the elucidation of key steps in the reaction pathway. The observed regioselectivity seems to be connected to the irreversible formation of a key α-imino gold carbene intermediate, common to all reaction profiles, through the initial regioselective nucleophilic attack of the anthranil N atom onto the alkyne fragment. © 2022 The Authors. Journal of Physical Organic Chemistry published by John Wiley & Sons Ltd.
ER -