Tandem Carbannulation of Blaise Reaction Intermediates

Paul Knochel; Diana Haas

doi:10.1055/s-0034-1378485

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Synfacts 2014; 10(8): 0854
DOI: 10.1055/s-0034-1378485

Metal-Mediated Synthesis

Tandem Carbannulation of Blaise Reaction Intermediates

Contributor(s):

Paul Knochel

,

Diana Haas

Sakthivel K, Srinivasan K * Bharathidasan University, India
Synthesis of Naphthalene Amino Esters by the Blaise Reaction of o-Alkynylarenenitriles.

J. Org. Chem. 2014;
79: 3244-3248

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Further Information

Publication History

Publication Date:
18 July 2014 (online)

Abstract
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Key words

Blaise reaction - naphthalenes - zinc - Reformatsky reagents

Significance

Herein, the authors report a convenient protocol for the synthesis of naphthalene amino esters starting from various o-alkynylarenenitriles and Reformatsky reagents via in situ generated Blaise reaction intermediates.

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Comment

The resulting Blaise reaction intermediates act as carbon nucleophiles and attack the triple bond via a tandem 6-endo-dig carbannulation providing the expected products in a highly chemo- and regioselective manner.

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