Dual Catalysis in Domino N‐Benzylation/Intramolecular C–H Arylation: Regio‐ and Chemoselective Synthesis of Annelated Nitrogen Heterocycles. Issue 25 (21st July 2014)

• Record Type: Journal Article
• Authors: Laha, Joydev K.; Dayal, Neetu; Singh, Swati; Bhimpuria, Rohan
• Is Part Of: European journal of organic chemistry. Issue 25(2014)
• Page Start: 5469
• Page End: 5475
• Publication Date: 2014-07-21
• Subjects: Domino reactions -- Nitrogen heterocycles -- Palladium -- Regioselectivity -- Chemoselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402395
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A general method has been developed for the synthesis of fused nitrogen heterocycles by using a domino N ‐benzylation/C–H arylation reaction sequence. The details and yields of the domino process were compared with those of the two‐step literature protocol. Fused azaindoles, which are otherwise difficult to obtain, were synthesized by using this process. The unprecedented catalytic role of PPh3 in this N ‐benzylation is described. Abstract : A regio‐ and chemoselective synthesis of fused nitrogen heterocycles is described that proceeds through a domino N ‐benzylation/C–H arylation reaction sequence. The dual catalysis of this domino process is supported by a mechanistic study.