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. 2017 Jul 7;19(13):3612-3615.
doi: 10.1021/acs.orglett.7b01588. Epub 2017 Jun 12.

Direct Conversion of Carboxylic Acids to Alkyl Ketones

Javad Amani  1 , Gary A Molander  1
Affiliations

Direct Conversion of Carboxylic Acids to Alkyl Ketones

Javad Amani et al. Org Lett. .

Abstract

An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carboxylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Photoredox/Ni dual catalysis cross-coupling of carboxylic acids with alkyltrifluoroborates.
Figure 2
Figure 2
Proposed mechanism for the acyl-sp3 cross-coupling.
Scheme 1
Scheme 1. Scope of Potassium Alkyltrifluoroborates in Cross-Coupling with Carboxylic Acids
See Supporting Information for experimental details. All cited yields are isolated. Reaction performed on 7.0 mmol scale with 1.5 mol % of Ir photocatalyst 1 and 3.0 mol % of [Ni(dtbbpy)(H2O)4]Cl2.
See this image and copyright information in PMC

References

    1. Huston R. C.; Bailey D. L. J. Am. Chem. Soc. 1946, 68, 1382.10.1021/ja01211a504. - DOI
    2. House H. O.; Bare T. M. J. Org. Chem. 1968, 33, 943.10.1021/jo01267a003. - DOI
    3. Suga K.; Watanabe S.; Fujita T.; Takahashi Y. Aust. J. Chem. 1973, 26, 2123.10.1071/CH9732123. - DOI
    4. Levine R.; Karten M. J.; Kadunce W. M. J. Org. Chem. 1975, 40, 1770.10.1021/jo00900a020. - DOI
    1. Dubois J. E.; Boussu M.; Lion C. Tetrahedron Lett. 1971, 12, 829.10.1016/S0040-4039(01)96567-0. - DOI
    2. Dieter R. K.; Sharma R. R.; Yu H.; Gore V. K. Tetrahedron 2003, 59, 1083.10.1016/S0040-4020(02)01526-0. - DOI
    1. Cahiez G.; Laboue B. Tetrahedron Lett. 1989, 30, 7369.10.1016/S0040-4039(00)70699-X. - DOI
    2. Cahiez G.; Laboue B. Tetrahedron Lett. 1992, 33, 4439.10.1016/S0040-4039(00)60104-1. - DOI
    3. Cahiez G.; Razafintsalama L.; Laboue B.; Chau F. Tetrahedron Lett. 1998, 39, 849.10.1016/S0040-4039(97)10747-X. - DOI
    1. Blaise E. E.; Maire M. Compt. Rend. 1907, 145, 73.
    2. Blaise E. E.; Koehler A. Bull. Soc. Chim. Paris 1910, 7, 215.
    3. Blaise E. E. Bull. Soc. Chim. 1911, 9, 1.
    4. Reddy C. K.; Knochel P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1700.10.1002/anie.199617001. - DOI
    1. Hart D. W.; Schwartz J. J. Am. Chem. Soc. 1974, 96, 8115.10.1021/ja00833a048. - DOI

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