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Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Abstract:

Efficient syntheses of 4,5-, 5,6-, and 6,7-indolyne precursors beginning from commercially available hydroxyindole derivatives are reported. The synthetic routes are versatile and allow access to indolyne precursors that remain unsubstituted on the pyrrole ring. Indolynes can be generated under mild fluoride-mediated conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with var...

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Publication status:
Published

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Publisher copy:
10.1021/ja1086485

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Journal:
Journal of the American Chemical Society
Volume:
132
Issue:
50
Pages:
17933-17944
Publication date:
2010-12-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:d5e95ad8-f2d7-4e7b-aedb-8ed7a30c0390
Source identifiers:
117660
Local pid:
pubs:117660
Language:
English
Keywords:

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