Chemoselective Reduction of the Carbonyl Functionality through Hydrosilylation: Integrating Click Catalysis with Hydrosilylation in One Pot

Herein we report the chemoselective reduction of the carbonyl functionality via hydrosilylation using a copper­(I) catalyst bearing the abnormal N-heterocyclic carbene <b>1</b> with low (0.25 mol %) catalyst loading at ambient temperature in excellent yield within a very short reaction time. The hydrosilylation reaction of α,β-unsaturated carbonyl compounds takes place selectively toward 1,2-addition (CO) to yield the corresponding allyl alcohols in good yields. Moreover, when two reducible functional groups such as imine and ketone groups are present in the same molecule, this catalyst selectively reduces the ketone functionality. Further, <b>1</b> was used in a consecutive fashion by combining the Huisgen cycloaddition and hydrosilylation reactions in one pot, yielding a range of functionalized triazole substituted alcohols in excellent yields

Halo-Bridged Abnormal NHC Palladium(II) Dimer for Catalytic Dehydrogenative Cross-Coupling Reactions of Heteroarenes

This work describes the dehydrogenative coupling of heteroarenes using a dimeric halo-bridged palladium­(II) catalyst bearing an abnormal NHC (<i>a</i>NHC) backbone. The catalyst can successfully activate the C–H bond of a wide range of heteroarenes, which include benzothiazole, benzoxazole, thiophene, furan, and <i>N</i>-methylbenzimidazole. Further, it exhibited good activity for heteroarenes bearing various functional groups such as CN, CHO, Me, OMe, OAc, and Cl. Additionally, we isolated the active catalyst by performing stoichiometric reaction and characterized it as the acetato-bridged dimer of (<i>a</i>NHC)­PdOAc by single-crystal X-ray study

Halo-Bridged Abnormal NHC Palladium(II) Dimer for Catalytic Dehydrogenative Cross-Coupling Reactions of Heteroarenes

This work describes the dehydrogenative coupling of heteroarenes using a dimeric halo-bridged palladium­(II) catalyst bearing an abnormal NHC (<i>a</i>NHC) backbone. The catalyst can successfully activate the C–H bond of a wide range of heteroarenes, which include benzothiazole, benzoxazole, thiophene, furan, and <i>N</i>-methylbenzimidazole. Further, it exhibited good activity for heteroarenes bearing various functional groups such as CN, CHO, Me, OMe, OAc, and Cl. Additionally, we isolated the active catalyst by performing stoichiometric reaction and characterized it as the acetato-bridged dimer of (<i>a</i>NHC)­PdOAc by single-crystal X-ray study