Unless otherwise noted, all manipulations are carried
out in either
a nitrogen-filled glovebox or under nitrogen using standard Schlenk
techniques. Reaction solvents were sparged with nitrogen and then
dried by passage through a column of activated alumina using an apparatus
purchased from Anhydrous Engineering. Deuterated benzene and chloroform
and toluene were purchased from Aldrich Chemical Company. Acetone,
benzyl bromide, 1,8-diaminonaphthalene, formic acid, LiAlH4, MeLi, KN(SiMe3)2, triethylorthoformate, and
Pd(OAc)2 were purchased from Aldrich Chemical Company and
used without further purification. 1-Isopropylperimidine, C10H6N(iPrN)CH, 1-isopropyl-3-benzylperimidinium
bromide,2 , and 1,3-isopropylperimidine-2-ylidene, 3 , were prepared by literature methods.22 (link),54 (link)1H spectra were run on either a Bruker 300, 400,
or
600 MHz spectrometer, and 13C{1H} NMR spectra
were run on either a Bruker 75, 100, or 150 MHz spectrometer using
the residual protons of the deuterated solvent for reference. Elemental
analyses were performed by Midwest Micro lab in Indianapolis, IN,
USA. High-resolution lock mass accuracy mass spectrometry was conducted
on an electrospray global quadrupole time-of-flight spectrometer at
the John L Holmes Mass Spectrometry Facility at the University of
Ottawa.
out in either
a nitrogen-filled glovebox or under nitrogen using standard Schlenk
techniques. Reaction solvents were sparged with nitrogen and then
dried by passage through a column of activated alumina using an apparatus
purchased from Anhydrous Engineering. Deuterated benzene and chloroform
and toluene were purchased from Aldrich Chemical Company. Acetone,
benzyl bromide, 1,8-diaminonaphthalene, formic acid, LiAlH4, MeLi, KN(SiMe3)2, triethylorthoformate, and
Pd(OAc)2 were purchased from Aldrich Chemical Company and
used without further purification. 1-Isopropylperimidine, C10H6N(iPrN)CH, 1-isopropyl-3-benzylperimidinium
bromide,
or
600 MHz spectrometer, and 13C{1H} NMR spectra
were run on either a Bruker 75, 100, or 150 MHz spectrometer using
the residual protons of the deuterated solvent for reference. Elemental
analyses were performed by Midwest Micro lab in Indianapolis, IN,
USA. High-resolution lock mass accuracy mass spectrometry was conducted
on an electrospray global quadrupole time-of-flight spectrometer at
the John L Holmes Mass Spectrometry Facility at the University of
Ottawa.