TY - JOUR
T1 - Double C-H Functionalization to Construct Polycyclic Heteroarenes Catalyzed by an Ionic Salt of a Pd Complex with an N-Heterocyclic Carbene Ligand
AU - Ghosh, Sanjay Kumar
AU - Kuo, Bing Chiuan
AU - Chen, Hsiang Yu
AU - Li, Jia Ying
AU - Liu, Shuang De
AU - Lee, Hon Man
PY - 2015/7/1
Y1 - 2015/7/1
N2 - A new ionic salt, cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2 (A), in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared by the salt metathesis reaction between [Pd(L)(PPh3)Cl2] and AgOTf in wet acetonitrile. It was successfully characterized by NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. Complex A was found to be effective in catalyzing the double C-H functionalization of various nitrogen- and sulfur-containing heteroarenes to form fused polycyclic heteroaromatic compounds with alkynes in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide. Indoles, thiophenes, imidazo[1,2-a]pyridine, and imidazoles were used as substrates. In particular, intriguing imidazo[5,1,2-cd]indolizine compounds could be obtained under the conditions employed. The complex cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2, in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared. This complex was effective in catalyzing the double C-H functionalization of various nitrogen- and sulfur-containing heteroarenes to form fused polycyclic heteroaromatic compounds with alkynes in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide.
AB - A new ionic salt, cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2 (A), in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared by the salt metathesis reaction between [Pd(L)(PPh3)Cl2] and AgOTf in wet acetonitrile. It was successfully characterized by NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. Complex A was found to be effective in catalyzing the double C-H functionalization of various nitrogen- and sulfur-containing heteroarenes to form fused polycyclic heteroaromatic compounds with alkynes in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide. Indoles, thiophenes, imidazo[1,2-a]pyridine, and imidazoles were used as substrates. In particular, intriguing imidazo[5,1,2-cd]indolizine compounds could be obtained under the conditions employed. The complex cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2, in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared. This complex was effective in catalyzing the double C-H functionalization of various nitrogen- and sulfur-containing heteroarenes to form fused polycyclic heteroaromatic compounds with alkynes in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide.
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U2 - 10.1002/ejoc.201500417
DO - 10.1002/ejoc.201500417
M3 - Article
AN - SCOPUS:85027919580
VL - 2015
SP - 4131
EP - 4142
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 19
ER -