Copper-catalyzed intermolecular C(sp3)-H bond functionalization towards the synthesis of tertiary carbamates.

Copper-catalyzed intermolecular C(sp3)–H bond functionalization towards the synthesis of tertiary carbamates† †Dedicated to Professor Iwao Ojima on his 70th birthday. ‡ ‡Electronic supplementary information (ESI) available: Experimental procedures, characterization data, and 1H and 13C NMR charts. See DOI: 10.1039/c5sc00238a

Ligand-Mediated and Copper-Catalyzed C(sp3)-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions

A novel and convenient copper (II) bromide and 1,8-diazabicyclo[5.4.1]undec-7-ene (DBU) or 1,10-phenanthroline catalysis protocol for the construction of α-alkyl-β-keto sulfones via C(sp(3))-H bond functionalization followed by C(sp(3))-S bond formation between aryl ketones and sodium sulfinates at room temperature has been developed. This method is applicable to a wide range of aryl ketones an...

Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C-H and N-H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of e...

[1+1+1] Cyclotrimerization for the Synthesis of Cyclopropanes

The synthesis of small rings by functionalization of C(sp(3) )-H bonds remains a great challenge. We report for the first time a copper-catalyzed [1+1+1] cyclotrimerization of acetophenone derivatives under mild reaction conditions. The reaction has a broad scope for the stereoselective synthesis of cyclopropanes by trimerization of acetophenone. The developed transformation is based on an extr...

Copper-catalyzed tandem aryl-halogen hydroxylation and CH2Cl2-based N,O-acetalization toward the synthesis of 2,3-dihydrobenzoxazinones.

The concise synthesis of 2,3-dihydro-4H-benzo[e][1,3]oxazin-4-ones has been accomplished by copper-catalyzed tandem reactions of o-halobenzamides, LiOH and dichloromethane. The aryl-halogen bond hydroxylation and subsequent N,O-acetalization on CH2Cl2 are enabled under catalytic conditions which allows the generation of C(sp2)-O, C(sp3)-O and C(sp3)-N bonds to give the target products.