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Rhodium(III)-catalyzed C-H activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group.
Chemistry. 2014 Feb 17; 20(8):2352-6.C

Abstract

An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for Rh(III)-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and C=O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DG(auto)). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DG(auto) strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zheng L
Key Laboratory of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084 (P.R. China).
Hua R
No affiliation info available

MeSH

CatalysisHeterocyclic CompoundsHydrazonesIndolesIsoquinolinesMolecular StructureRhodium

Pub Type(s)

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

Language

eng

PubMed ID

24458554

Citation

Zheng, Liyao, and Ruimao Hua. "Rhodium(III)-catalyzed C-H Activation and Indole Synthesis With Hydrazone as an Auto-formed and Auto-cleavable Directing Group." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 8, 2014, pp. 2352-6.
Zheng L, Hua R. Rhodium(III)-catalyzed C-H activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group. Chemistry. 2014;20(8):2352-6.
Zheng, L., & Hua, R. (2014). Rhodium(III)-catalyzed C-H activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(8), 2352-6. https://doi.org/10.1002/chem.201304302
Zheng L, Hua R. Rhodium(III)-catalyzed C-H Activation and Indole Synthesis With Hydrazone as an Auto-formed and Auto-cleavable Directing Group. Chemistry. 2014 Feb 17;20(8):2352-6. PubMed PMID: 24458554.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(III)-catalyzed C-H activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group. AU - Zheng,Liyao, AU - Hua,Ruimao, Y1 - 2014/01/23/ PY - 2013/11/03/received PY - 2014/1/25/entrez PY - 2014/1/25/pubmed PY - 2015/1/13/medline KW - CH activation KW - NN cleavage KW - hydrazones KW - indoles KW - rhodium catalysis SP - 2352 EP - 6 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 8 N2 - An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for Rh(III)-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and C=O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DG(auto)). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DG(auto) strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24458554/Rhodium_III__catalyzed_C_H_activation_and_indole_synthesis_with_hydrazone_as_an_auto_formed_and_auto_cleavable_directing_group_ DB - PRIME DP - Unbound Medicine ER -