Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes

Devarapalli, R K and G, Satyanarayana (2015) Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes. Organic Letters, 17 (23). pp. 5894-5897. ISSN 1523-7060

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Abstract

A domino [Pd]-catalysis for the efficient synthesis of fluorenones is presented. The overall reaction proceeds through the formation of a five membered Pd(II)-cycle via a highly regioselective ortho C(sp2)-H activation(s) of simple benzylamine that combines with external iodo arenes to give ortho arylated products. Significantly, the reaction further activates the C(sp3)-H and C(sp2)-H (intramolecular oxidative Heck coupling) bonds to give tricyclic imine systems. Then the usual water workup affords the fused tricyclic ketones (fluorenones). Remarkably, this one-pot operation enabled the effective construction of two C–C to three C–C bonds

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IITH Creators:
IITH CreatorsORCiD
G, SatyanarayanaUNSPECIFIED
Item Type: Article
Additional Information: We are thankful to Dr. G. Prabusankar and Dr. T. K. Panda, Department of Chemistry, Indian Institute of Technology, Hyderabad, for their inputs on the X-ray crystal structures.
Uncontrolled Keywords: iodo arenes, one-pot operation, tricyclic ketones
Subjects: Chemistry > Organic chemistry
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Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 18 Dec 2015 05:21
Last Modified: 18 Dec 2015 05:21
URI: http://raiith.iith.ac.in/id/eprint/2084
Publisher URL: http://dx.doi.org/10.1021/acs.orglett.5b03077
OA policy: http://www.sherpa.ac.uk/romeo/issn/1523-7060/
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