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Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation.
J Am Chem Soc. 2017 11 15; 139(45):16080-16083.JA

Abstract

We report Pd(II)-catalyzed β-C(sp3)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp3)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls.

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Authors+Show Affiliations

Zhu RY
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
Liu LY
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
Park HS
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
Hong K
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
Wu Y
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
Senanayake CH
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , Ridgefield, Connecticut 06877, United States.
Yu JQ
Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.

MeSH

AlkylationAminooxyacetic AcidCatalysisHydrocarbons, AromaticIodidesKetonesPalladium

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29086554

Citation

Zhu, Ru-Yi, et al. "Versatile Alkylation of (Hetero)Aryl Iodides With Ketones Via β-C(sp3)-H Activation." Journal of the American Chemical Society, vol. 139, no. 45, 2017, pp. 16080-16083.
Zhu RY, Liu LY, Park HS, et al. Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation. J Am Chem Soc. 2017;139(45):16080-16083.
Zhu, R. Y., Liu, L. Y., Park, H. S., Hong, K., Wu, Y., Senanayake, C. H., & Yu, J. Q. (2017). Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation. Journal of the American Chemical Society, 139(45), 16080-16083. https://doi.org/10.1021/jacs.7b09761
Zhu RY, et al. Versatile Alkylation of (Hetero)Aryl Iodides With Ketones Via β-C(sp3)-H Activation. J Am Chem Soc. 2017 11 15;139(45):16080-16083. PubMed PMID: 29086554.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp3)-H Activation. AU - Zhu,Ru-Yi, AU - Liu,Luo-Yan, AU - Park,Han Seul, AU - Hong,Kai, AU - Wu,Yongwei, AU - Senanayake,Chris H, AU - Yu,Jin-Quan, Y1 - 2017/11/03/ PY - 2017/11/1/pubmed PY - 2018/1/3/medline PY - 2017/11/1/entrez SP - 16080 EP - 16083 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 139 IS - 45 N2 - We report Pd(II)-catalyzed β-C(sp3)-H (hetero)arylation of a variety of ketones using a commercially available 2,2-dimethyl aminooxyacetic acid auxiliary. Facile installation and removal of the auxiliary as well as its superior scope for both ketones and (hetero)aryl iodides overcome the significant limitations of the previously reported β-C(sp3)-H arylation of ketones. The ready availability of ketones renders this reaction a broadly useful method for alkyl-(hetero)aryl coupling involving both primary and secondary alkyls. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/29086554/Versatile_Alkylation_of__Hetero_Aryl_Iodides_with_Ketones_via_β_C_sp3__H_Activation_ DB - PRIME DP - Unbound Medicine ER -