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Novel Carbazole‐Based N ‐Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd‐Catalyzed Coupling Processes
Author(s) -
Girase Tejpalsingh Ramsingh,
Kapdi Anant R.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900419
Subject(s) - chemistry , carbene , borylation , carbazole , combinatorial chemistry , catalysis , heck reaction , tandem , resveratrol , cascade reaction , organic chemistry , palladium , aryl , alkyl , materials science , biochemistry , composite material
A series of new carbazole‐based N ‐heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole‐based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale‐up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double‐tandem chemoselective Heck reaction followed by Miyaura borylation in a one‐pot procedure to give single‐step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple‐tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one‐pot modification of biologically relevant molecules.