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Hydrogen‐Bonding Pincer Complexes with Two Protic N‐Heterocyclic Carbenes from Direct Metalation of a 1,8‐Bis(imidazol‐1‐yl)carbazole by Platinum, Palladium, and Nickel
Author(s) -
Marelius David C.,
Darrow Evan H.,
Moore Curtis E.,
Golen James A.,
Rheingold Arnold L.,
Grotjahn Douglas B.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501945
Subject(s) - chemistry , metalation , pincer movement , trifluoromethanesulfonate , medicinal chemistry , palladium , carbene , intramolecular force , hydrogen bond , photochemistry , polymer chemistry , catalysis , organic chemistry , molecule
Pincer protic N‐heterocyclic carbene (PNHC) complexes were synthesized by direct metalation, the formation of a metal carbon bond from an unfunctionalized CH bond in a single synthetic step. Significantly, direct metalation succeeded even for a first‐row metal, nickel. The chloride complexes were isolated and then converted to the acetate, triflate, or in the platinum case, a hydride analogue. Crystal structures and 1 H, 13 C, and 15 N NMR data, as well as IR spectra, document the effects of intramolecular hydrogen bonding and the planar but flexible pincer framework. Anti‐Markovnikov addition of OH bonds to alkynes, including catalyzed alkyne hydration, were demonstrated on the Pt triflate analog.