Amide directed selectivity switch in distal C-H arylation of α-naphthoic acids

doi:10.21203/rs.3.rs-1503504/v1

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Amide directed selectivity switch in distal C-H arylation of α-naphthoic acids

https://doi.org/10.21203/rs.3.rs-1503504/v1

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posted 07 Apr, 2022

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Remote C4-H functionalization of a-naphthoic acids is highly challenging due to the presence of proximally more accessible C-H bonds at the C2and C8 positions. Herein, we report the first palladium-catalysed direct C4 arylation of 1-naphthamides with high regioselectivity and excellent functional group compatibility. The regioselectivity of this one-step reaction could be switched to the C7 position by simply changing the directing group under otherwise identical conditions. Diverse aryl couples were found compatible for both C4 and C7 arylation. Control experiments and kinetic studies were carried out to identify the mechanistic motives of the unique selectivity switch.

para-arylation of a-naphthamide: An oven-dried screw cap reaction tube was charged with a magnetic stir-bar, Pd(OAc)₂ (7 mol% 1.6 mg for 0.2 mmol), AgTFA (1.5 equiv., 33 mg), a-naphthamide (0.1 mmol, 25.5 mg) and aryl iodide (1.2 equiv., 0.12 mmol). Then 1 mL of HFIP was added. The reaction mixture was stirred vigorously on a preheated oil bath at 120 °C along. The reaction was carried out for 12 h and the reaction mixture was diluted with EtOAc and filtered through a celite pad. The desired arylation product was isolated by column chromatography using silica gel (100-200 mesh size) and petroleum ether/ethyl acetate as the eluent.

Data availability: The authors declare that the main data supporting the findings of this study are available within the article and its Supplementary information files. Further data are available from the corresponding author on request. Source data are provided with this paper.

Acknowledgements: We thank SERB India for funding to DM for carrying out this activity (Grant no. CRG/2018/003951). We would also like to acknowledge NSF (CHE-2029932), Robert A. Welch Foundation (D2034-20200401), and Texas Tech University for financial support.

Author contributions: SKP, JPB and ME performed of the experiments. DM and HG supervised and directed the progress. JPB, SKP, ME, HG and DM prepared the manuscript.

Funding: This activity was supported by SERB, India (CRG/2018/003951), NSF (CHE-2029932), Robert A. Welch Foundation (D2034-20200401).

Competing interests: The authors declare no competing interests.

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There is NO Competing Interest.

SupportingInformation.pdf
Supporting Files
Cif3ab.cif
Cif_3ab
Cif3ac.cif
Cif_3ac
Cif3ai.cif
Cif_3ai
Cif3aj.cif
Cif_3aj
Cif3al.cif
Cif_3al
Cif3f.cif
Cif_3f
Cif3g.cif
Cif_3g
Cif3j.cif
Cif_3j
Cif3k.cif
Cif_3k
Cif3x.cif
Cif_3x
Cif3y.cif
Cif_3y
Cif6h.cif
Cif_6h
Cif9d.cif
Cif_9d
NCOMMS2211960crystallography.zip
CIF and checkcif files crystallography

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Amide directed selectivity switch in distal C-H arylation of α-naphthoic acids

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