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Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: concise synthesis of indole derivatives.
Org Lett. 2012 Aug 17; 14(16):4270-3.OL

Abstract

Synthesis of the indole skeleton was achieved using a Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp(3))-H activation. It was found that slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad(2)P(n)Bu is a good ligand for C(sp(3))-H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino reaction incorporating alkyne insertion.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nanjo T
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Tsukano C
No affiliation info available
Takemoto Y
No affiliation info available

MeSH

AlkynesCatalysisIndolesMolecular StructureNitrilesPalladium

Pub Type(s)

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

Language

eng

PubMed ID

22849720

Citation

Nanjo, Takeshi, et al. "Palladium-catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp3)-H Activation: Concise Synthesis of Indole Derivatives." Organic Letters, vol. 14, no. 16, 2012, pp. 4270-3.
Nanjo T, Tsukano C, Takemoto Y. Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: concise synthesis of indole derivatives. Org Lett. 2012;14(16):4270-3.
Nanjo, T., Tsukano, C., & Takemoto, Y. (2012). Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: concise synthesis of indole derivatives. Organic Letters, 14(16), 4270-3. https://doi.org/10.1021/ol302035j
Nanjo T, Tsukano C, Takemoto Y. Palladium-catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp3)-H Activation: Concise Synthesis of Indole Derivatives. Org Lett. 2012 Aug 17;14(16):4270-3. PubMed PMID: 22849720.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: concise synthesis of indole derivatives. AU - Nanjo,Takeshi, AU - Tsukano,Chihiro, AU - Takemoto,Yoshiji, Y1 - 2012/07/31/ PY - 2012/8/2/entrez PY - 2012/8/2/pubmed PY - 2012/12/10/medline SP - 4270 EP - 3 JF - Organic letters JO - Org Lett VL - 14 IS - 16 N2 - Synthesis of the indole skeleton was achieved using a Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp(3))-H activation. It was found that slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad(2)P(n)Bu is a good ligand for C(sp(3))-H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino reaction incorporating alkyne insertion. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22849720/Palladium_catalyzed_cascade_process_consisting_of_isocyanide_insertion_and_benzylic_C_sp3__H_activation:_concise_synthesis_of_indole_derivatives_ L2 - https://doi.org/10.1021/ol302035j DB - PRIME DP - Unbound Medicine ER -