The Development of Domino Reactions Incorporating the Heck Reaction: The Formation of N-Heterocycles

• Published in: European Journal of Organic Chemistry Vol. 2012; no. 3; pp. 544 - 558
• Main Authors: Rixson, James E., Chaloner, Thomas, Heath, Charles H., Tietze, Lutz F., Stewart, Scott G.
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Cascade ­reactions; Catalysis; Catalytic reactions; Chemistry; Chemistry, Organic; Domino reactions; Exact sciences and technology; General and physical chemistry; Homogeneous catalysis; Kinetics and mechanisms; Nitrogen heterocycles; Organic chemistry; Palladium; Physical Sciences; Reactivity and mechanisms; Science & Technology; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; COMPLEX; PALLADACYCLES; ALLYLATION; EFFICIENT SYNTHESIS; TERMINAL ALKYNES; Palladium; Cascade reactions; INDOLES; Nitrogen heterocycles; Homogeneous catalysis; Domino reactions; ARYL IODIDES; DERIVATIVES; CYCLIZATION; Catalytic reaction; Nitrogen heterocycle; Buchwald-Hartwig reaction; Heck reaction; Transition metal; Buchwald Hartwig reaction; Platinoid; Successive reaction
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201101305

The methodological development of a series of domino or cascade reactions affording a series of N‐heterocycles is described. The rapid formation of these ring systems is in each case associated with the incorporation of a Heck reaction at either an early or a late stage of the domino process. A range of catalytic conditions and substrate modifications for optimisation of domino Tsuji–Trost/Heck, Buchwald–Hartwig/Heck and Heck/carbopalladation reaction sequences are reported. The development of a series of domino or cascade reactions affording a collection of N‐heterocycles is described. In each of the processes a palladium‐catalysed Heck cross‐coupling reaction in utilised to produce the desired ring system efficiently.