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. 2011 May 6;13(9):2452-5.
doi: 10.1021/ol200693d. Epub 2011 Apr 11.

Fluorenone synthesis by palladacycle-catalyzed sequential reactions of 2-bromobenzaldehydes with arylboronic acids

Tao-Ping Liu  1 , Yuan-Xi Liao, Chun-Hui Xing, Qiao-Sheng Hu
Affiliations

Fluorenone synthesis by palladacycle-catalyzed sequential reactions of 2-bromobenzaldehydes with arylboronic acids

Tao-Ping Liu et al. Org Lett. .

Abstract

A new, anionic four-electron donor-based (type I) palladacycle-catalyzed sequential reaction of 2-bromobenzaldehydes with arylboronic acids based on the addition reaction, cyclization via C-H activation-oxidation sequence is described. Our study provided an efficient access to a variety of substituted fluorenones/indenofluorenediones from readily available arylboronic acids and 2-bromobenzaldehydes.

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Figures

Figure 1
Figure 1
Type I Palladacycles
Scheme 1
Scheme 1
Type I Palladacycles as Double Catalysts for a New Sequential Reaction Based on the Addition Reaction, Cyclization via C-H Activation, and Oxidation Sequence
Scheme 2
Scheme 2
Type I Palladacycle-Catalyzed Indenofluorenedione preparation by the New Sequential Reaction
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References

    1. Tietze LF, Brasche G, Gericke K. Domino Reactions in Organic Synthesis. Weinheim, Germany: Wiley-VCH; 2006.

    1. For recent reviews on sequential reactions, see: Nicolaou KC, Chen JS. Chem. Soc. Rev. 2009;38:2993–3009. Kirsch SF. Synthesis. 2008:3183–3204. Nicolaou KC, Edmonds DJ, Bulger PG. Angew. Chem., Int. Ed. 2006;45:7134–7186. Wasilke J-C, Obrey SJ, Baker T, Bazan GC. Chem. Rev. 2005;105:1001–1020. Tietze LF. Chem. Rev. 1996;96:115–136.

    1. For recent reviews: Dupont J, Consorti CS, Spencer J. Chem. Rev. 2005;105:2527–2572. Beletskaya IP, Cheprakov AV. J. Organomet. Chem. 2004;689:4055–4082. Bedford RB. Chem. Commun. 2003:1787–1796. Newkome GR, Puckett WE, Gupta VK, Kiefer GE. Chem. Rev. 1986;86:451–489.

    1. Most Type I palladacycles are known to exist as bridged dimers and to dissociate into monomeric forms during reactions. Type I palladacycles in this paper were drawn in monomeric forms.

    1. For recent reviews on transition metal-catalyzed addition reactions of organoborons with carbonyl-containing compounds: Miyaura N. Synlett. 2009:2039–2050. Gutnov A. Eur. J. Org. Chem. 2008:4547–4554. Glorius F. Angew. Chem., Int. Ed. 2004;43:3364–3366. Hayashi T, Yamasaki K. Chem. Rev. 2003;103:2829–2844. Fagnou K, Lautens M. Chem. Rev. 2003;103:169–196. and references cited therein.

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