Journal
SYNTHESIS-STUTTGART
Volume 50, Issue 17, Pages 3420-3429Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1591594
Keywords
2-pyridone; iridium-catalyzed borylation; C-H functionalization; CC4; cytisine
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Funding
- Royal Thai Government
- University of Bristol
- EPSRC [EP/N024117/1]
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
- EPSRC [EP/N024117/1, EP/K03927X/1] Funding Source: UKRI
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The high regioselectivity associated with the iridium-catalysed borylation of pyridones has been exploited to provide a very direct and efficient entry to C(10) doubly substituted CC4 variants of cytisine. Two approaches have been evaluated based on (i) C-H activation of cytisine (or an N-substituted derivative) followed by N-alkylation (to enable dimer formation) and (ii) direct C-H activation and borylation of CC4 itself. Both approaches provide access to C(10)-functionalized CC4 derivatives, but direct borylation of CC4 allows for a wider range of functional group interconversions to be tolerated.
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