Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group

Xiao Yang Chen; Seyma Ozturk; Erik J. Sorensen

doi:10.1021/acs.orglett.7b00161

Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group

Xiao Yang Chen
, Seyma Ozturk
, Erik J. Sorensen

Chemistry

Research output: Contribution to journal › Article › peer-review

108 Scopus citations

Abstract

The first synthesis of substituted fluorenones directly from benzaldehydes and aryl iodides via a Pd(II)-catalyzed C(sp²)-H functionalization cascade is reported. Featuring anthranilic acid as an inexpensive transient directing group, the process is compatible with a variety of benzaldehydes and aryl iodides. A three-step synthesis of the antiviral drug Tilorone was completed in an excellent overall yield (40%), demonstrating the utility of this method.

Original language	English (US)
Pages (from-to)	1140-1143
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.7b00161
State	Published - Mar 3 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b00161

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abstract = "The first synthesis of substituted fluorenones directly from benzaldehydes and aryl iodides via a Pd(II)-catalyzed C(sp2)-H functionalization cascade is reported. Featuring anthranilic acid as an inexpensive transient directing group, the process is compatible with a variety of benzaldehydes and aryl iodides. A three-step synthesis of the antiviral drug Tilorone was completed in an excellent overall yield (40\%), demonstrating the utility of this method.",

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Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group

Abstract

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