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Iridium(III) Photocatalysis: A Visible‐Light‐Induced Dearomatizative Tandem [4+2] Cyclization to Furnish Benzindolizidines
Author(s) -
Mühmel Sandra,
Alpers Dirk,
Hoffmann Frank,
Brasholz Malte
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502572
Subject(s) - photocatalysis , tandem , annulation , visible spectrum , photochemistry , iridium , chemistry , yield (engineering) , intermolecular force , hydrogen atom , irradiation , catalysis , materials science , organic chemistry , molecule , optoelectronics , group (periodic table) , physics , nuclear physics , metallurgy , composite material
A photocatalytic dearomatizative tandem [4+2] cyclization between N ‐(2‐iodoethyl)indoles and a variety of alkenes leads to tri‐ and tetracyclic benzindolizidines with high diastereoselectivity and yield. The intermolecular annulation reaction is performed under visible‐light irradiation and employs [Ir(ppy) 3 ] or [Ir(dtbbpy)(ppy) 2 ] PF 6 as photocatalysts, in combination with tertiary amines as electron and hydrogen atom donors.