Iridium-Catalysed C-H Borylation of 2-Pyridones; Bisfunctionalisation of CC4

Aurélien Honraedt; Worawat Niwetmarin; Cecilia Gotti; Hugo Rego Campello; Timothy Gallagher

doi:10.1055/s-0036-1591594

Iridium-Catalysed C-H Borylation of 2-Pyridones; Bisfunctionalisation of CC4

Aurélien Honraedt, Worawat Niwetmarin, Cecilia Gotti, Hugo Rego Campello^*, Timothy Gallagher

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

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.

Original language	English
Article number	ss-2018-t0235-op
Pages (from-to)	3420-3429
Number of pages	10
Journal	Synthesis (Germany)
Volume	50
Issue number	17
Early online date	29 Jun 2018
DOIs	https://doi.org/10.1055/s-0036-1591594
Publication status	Published - 29 Jun 2018

Keywords

2-pyridone
C-H functionalization
CC4
cytisine
iridium-catalyzed borylation

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title = "Iridium-Catalysed C-H Borylation of 2-Pyridones; Bisfunctionalisation of CC4",

abstract = "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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T1 - Iridium-Catalysed C-H Borylation of 2-Pyridones; Bisfunctionalisation of CC4

AU - Honraedt, Aurélien

AU - Niwetmarin, Worawat

AU - Gotti, Cecilia

AU - Campello, Hugo Rego

AU - Gallagher, Timothy

PY - 2018/6/29

Y1 - 2018/6/29

N2 - 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.

AB - 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.

KW - 2-pyridone

KW - C-H functionalization

KW - CC4

KW - cytisine

KW - iridium-catalyzed borylation

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U2 - 10.1055/s-0036-1591594

DO - 10.1055/s-0036-1591594

M3 - Article (Academic Journal)

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SN - 0039-7881

VL - 50

SP - 3420

EP - 3429

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 17

M1 - ss-2018-t0235-op

ER -

Iridium-Catalysed C-H Borylation of 2-Pyridones; Bisfunctionalisation of CC4

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