A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation†
Stephen P. Cooper
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.chm.bris.ac.uk/org/bmilburn/index2.htm
Search for more papers by this authorCorresponding Author
Prof. Dr. Kevin I. Booker-Milburn
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.chm.bris.ac.uk/org/bmilburn/index2.htm
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.chm.bris.ac.uk/org/bmilburn/index2.htmSearch for more papers by this authorStephen P. Cooper
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.chm.bris.ac.uk/org/bmilburn/index2.htm
Search for more papers by this authorCorresponding Author
Prof. Dr. Kevin I. Booker-Milburn
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.chm.bris.ac.uk/org/bmilburn/index2.htm
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK) http://www.chm.bris.ac.uk/org/bmilburn/index2.htmSearch for more papers by this authorWe thank the EPSRC Bristol Chemical Synthesis Doctoral Training Centre (EP/G036764/1) for a PhD studentship (S.P.C.) and Argenta for funding.
Graphical Abstract
Don't overdo it: A palladium(II)-catalyzed CH activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).
Abstract
Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed CH activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step.
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