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Palladium Acyclic Diaminocarbene (ADC) Triflate Complexes as Effective Precatalysts for the Hiyama Alkynylation/Cyclization Reaction Yielding Benzofuran Compounds: Probing the Influence of the Triflate Co‐Ligand in the One‐Pot Tandem Reaction
Author(s) -
Singh Chandan,
Prakasham A. P.,
Ghosh Prasenjit
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803292
Subject(s) - chemistry , trifluoromethanesulfonate , benzofuran , tandem , medicinal chemistry , aryl , ligand (biochemistry) , palladium , alkynylation , catalysis , cascade reaction , salt metathesis reaction , combinatorial chemistry , organic chemistry , metathesis , polymer chemistry , stereochemistry , polymerization , alkyl , biochemistry , materials science , receptor , composite material , polymer
Palladium acyclic diaminocarbene (ADC) complexes of the type cis ‐[(R 1 NH)(R 2 )methylidene]Pd(OCOCF 3 ) 2 (CNR 1 ) [R 1 = 2,4,6‐(CH 3 ) 3 C 6 H 2 : R 2 = NC 4 H 8 ( 1 ); NC 5 H 10 ( 2 )] have been synthesized and structurally characterized. These 1 and 2 complexes are effective precatalysts for the one‐pot tandem Hiyama alkynylation/cyclization reaction producing benzofuran compounds and, quite interestingly, higher yields of ca . 33−52 % were observed for the aryl triethoxysilylalkyne substrates as compared to that of ca . 15−21 % for the aliphatic triethoxysilylalkyne substrates. The 1 and 2 complexes were conveniently prepared by the salt metathesis reaction of the chloro derivatives with AgOCOCF 3 in excellent yields ( ca . 84−94 %) under ambient conditions.