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

Full text not available from this repository. (Request a copy)

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

[error in script]

IITH Creators:

IITH Creators	ORCiD
G, Satyanarayana	UNSPECIFIED

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
?? sub5.8 ??

Divisions:

Department of Chemistry

Depositing User:

Team Library

Date Deposited:

18 Dec 2015 05:21

Last Modified:

18 Dec 2015 05:21