140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.

Catalytic Functionalization of Indoles in a New Dimension

3.1. Carbon−Nitrogen Bond Formation 14 3.1.

Cerium(IV) ammonium nitrate--a versatile single-electron oxidant.

Vor 140 Jahren schlug Adolf von Baeyer die Struktur fur eine heteroaromatische Verbindung vor, die die organische und medizinische Chemie nachhaltig veranderte: Indol. Nach mehr als einem Jahrhundert beeinflussen Indol selbst, ebenso wie naturliche Indolderivate, weitgehend die Entwicklung in der Synthesechemie. Vor allem die allgegenwartige Prasenz des Indolrings in pharmazeutischen und agrochemischen Verbindungen sowie seine Verwendung in der Materialchemie sind ausschlaggebend fur das anhaltende Interesse an der Entwicklung von neuen milden und effizienten Synthesestrategien fur funktionalisierte Indolderivate. Dieser Aufsatz fasst die Fortschritte hinsichtlich der selektiven katalytischen Funktionalisierung von Indolen (durch C-C-Kupplung) aus den vergangenen vier Jahre zusammen.

Katalytische Funktionalisierung von Indolen in einer neuen Dimension

Cerium(IV) Ammonium Nitrate as a Catalyst in Organic Synthesis

Ceric Ammonium Nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction

CAN and iodine-catalyzed reaction of indole or 1-methylindole with α,β-unsaturated ketone or aldehyde

CAN (cerium ammonium nitrate) and iodine can catalyze the reactions of indole or 1-methylindole with α,β-unsaturated ketone or aldehyde in DMSO/H2O (5:1) or ether solution at room temperature to obtain moderate to high yields of different products.

Wang Yi-Fu

Papers

CAN and iodine-catalyzed reaction of indole or 1-methylindole with α,β-unsaturated ketone or aldehyde

CAN- and Iodine-Catalyzed Reaction of Indole or 1-Methylindole with α,β-Unsaturated Ketone or Aldehyde.