Direct Arylation of Heteroarenes
Catalyzed by a Palladium-1,10-Phenanthroline
Complex

Ryo Takita; Daichi Fujita; Fumiyuki Ozawa

doi:10.1055/s-0030-1259727

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Synlett 2011(7): 959-963
DOI: 10.1055/s-0030-1259727

LETTER

Direct Arylation of Heteroarenes Catalyzed by a Palladium-1,10-Phenanthroline Complex

Ryo Takita*^a,b, Daichi Fujita^a, Fumiyuki Ozawa*^a
^a International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
Fax: +81(774)383039; e-Mail: ozawa@scl.kyoto-u.ac.jp;
^b Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
e-Mail: takita@mol.f.u-tokyo.ac.jp;

Weitere Informationen

Publikationsverlauf

Received 10 December 2010
Publikationsdatum:
10. März 2011 (online)

Abstract
Volltext
Referenzen
Zusatzmaterial

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Abstract

A new entry in direct arylation of heteroarenes using Pd(OAc)₂ and 1,10-phenanthroline as a nitrogen-based ligand is reported. The long induction period observed at the initial stage of the reaction was effectively reduced by modification of the catalyst preparation, leading to improved chemical yields (69-92%) and shortening of reaction times (3-10 h).

Key words

direct arylation - palladium - 1,10-phenanthroline - heteroarenes - biaryls

Supporting Information

References and Notes

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4

In this manuscript, the term ‘direct arylation of heteroarenes’ denotes the reaction of heteroarenes with (pseudo)halo-arenes. For other types of reactions (e.g., directing-group-controlled reactions or the reaction of arenes with organometallic reagents), see ref. 1.

16

Isolated Pd(OAc)₂(1,10-phenanthroline) gave a comparable result (69%) under the same conditions.

17

The remaining part of 1a is very probably converted to benzene. The reduction of 1e to give ethyl benzoate was confirmed by GC-MS analysis of the reaction solution of entry 5 in Table [²] .