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Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins.
Org Lett. 2015 Oct 02; 17(19):4850-3.OL

Abstract

We report here a method for direct catalytic introduction of simple α-acylalkyl groups via rhodium-catalyzed C-H functionalization with cyclic alkenyl carbonates, synthetic equivalents to enolates bearing leaving groups. The reaction proceeded smoothly without using bases to give α-aryl ketones in high yields. Various nitrogen-containing aromatic rings and amide groups serve as directing groups. 3-Substituted isocoumarins can also be prepared by one-pot C-H functionalization/cyclization.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hara Y
Department of Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan and.
Onodera S
Department of Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan and.
Kochi T
Department of Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan and.
Kakiuchi F
Department of Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan and. JST, ACT-C , 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

MeSH

AlkenesCarbonatesCatalysisCyclizationIsocoumarinsKetonesMolecular StructureNitrogenRhodium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26378654

Citation

Hara, Yusuke, et al. "Catalytic Formation of α-Aryl Ketones By C-H Functionalization With Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins." Organic Letters, vol. 17, no. 19, 2015, pp. 4850-3.
Hara Y, Onodera S, Kochi T, et al. Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins. Org Lett. 2015;17(19):4850-3.
Hara, Y., Onodera, S., Kochi, T., & Kakiuchi, F. (2015). Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins. Organic Letters, 17(19), 4850-3. https://doi.org/10.1021/acs.orglett.5b02414
Hara Y, et al. Catalytic Formation of α-Aryl Ketones By C-H Functionalization With Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins. Org Lett. 2015 Oct 2;17(19):4850-3. PubMed PMID: 26378654.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic Formation of α-Aryl Ketones by C-H Functionalization with Cyclic Alkenyl Carbonates and One-Pot Synthesis of Isocoumarins. AU - Hara,Yusuke, AU - Onodera,Shunsuke, AU - Kochi,Takuya, AU - Kakiuchi,Fumitoshi, PY - 2015/9/18/entrez PY - 2015/9/18/pubmed PY - 2016/1/16/medline SP - 4850 EP - 3 JF - Organic letters JO - Org Lett VL - 17 IS - 19 N2 - We report here a method for direct catalytic introduction of simple α-acylalkyl groups via rhodium-catalyzed C-H functionalization with cyclic alkenyl carbonates, synthetic equivalents to enolates bearing leaving groups. The reaction proceeded smoothly without using bases to give α-aryl ketones in high yields. Various nitrogen-containing aromatic rings and amide groups serve as directing groups. 3-Substituted isocoumarins can also be prepared by one-pot C-H functionalization/cyclization. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26378654/Catalytic_Formation_of_α_Aryl_Ketones_by_C_H_Functionalization_with_Cyclic_Alkenyl_Carbonates_and_One_Pot_Synthesis_of_Isocoumarins_ DB - PRIME DP - Unbound Medicine ER -