General solution: An efficient rhodium‐catalyzed dual CH bond activation and cyclization of N‐methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp*=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CC and CN bond formation under mild conditions afforded a wide range of substituted phenanthridinones 3.

An efficient o‐arylation of pivalamides by aryl iodides via rhodium(III)‐catalyzed C–H activation is demonstrated for the first time. Further, the biaryl products can be converted effectively into biologically active phenanthridine and phenanthridinone derivative.magnified image

A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C À H activation is described. The oxidant-free olefination reaction involves the in situ generation of an À N À N=CR 1 R 2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.

Universelle Lösung: Die effiziente Rhodium‐katalysierte duale C‐H‐Bindungsaktivierung und Cyclisierung von N‐Methoxybenzamiden 1 mit Arylboronsäuren 2 (siehe Schema; Cp*=Me5C5) bietet einen einfachen und universellen Zugang zur Phenanthridinonstruktur, die in Natur‐ und Wirkstoffen weit verbreitet ist. Hoch regioselektive C‐C‐ und C‐N‐Bindungsbildungen unter milden Bedingungen liefern ein breites Spektrum von substituierten Phenanthridinonen 3.

The reaction proceeds with high regioselectivity under mild conditions to afford a broad spectrum of substituted title compounds through C-C and C-N coupling. It can be extended to natural product synthesis. -(KARTHIKEYAN, J.; HARIDHARAN, R.; CHENG*, C.-H.; Angew. Chem., Int. Ed. 51 (2012) 49, 12343-12347, http://dx.doi.org/10.1002/anie.201206890 ; Dep. Chem., Natl. Tsing Hua Univ., Hsinchu 30013, Taiwan; Eng.) -Mais 22-168