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Palladium‐Catalyzed C2−H Arylation of Unprotected (N−H)‐Indoles “On Water” Using Primary Diamantyl Phosphine Oxides as a Class of Primary Phosphine Oxide Ligands
Author(s) -
Moncea Oana,
Poinsot Didier,
Fokin Andrey A.,
Schreiner Peter R.,
Hierso JeanCyrille
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800187
Subject(s) - phosphine , phosphine oxide , catalysis , chemistry , palladium , primary (astronomy) , oxide , combinatorial chemistry , surface modification , organic chemistry , medicinal chemistry , physics , astronomy
We present the Pd‐catalyzed arylation of (N−H)‐indoles with functionalized haloarenes “on water” using hitherto untested primary diamantyl phosphine oxides (PPO) as ligands. Remarkable C2−H arylation selectivity was achieved by employing functionalized iodoarenes and N‐unprotected indoles. We provide evidence that the in situ generated oxide of (9‐hydroxydiamant‐4‐yl)phosphine L1 is key for the reaction efficiency by comparing a set of diamantane‐based compounds structurally related to L1 . Our results demonstrate the power of the new PPO ligands for the C−H functionalization of unprotected (N−H)‐heterocycles.