Journal
ORGANIC LETTERS
Volume 16, Issue 22, Pages 6024-6027Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol5030508
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Funding
- NIGMS NIH HHS [R01 GM-081376, R01 GM081376] Funding Source: Medline
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The synthesis of 2-(chloromethyl)-2,1-borazaronaphthalene has provided an opportunity to expand dramatically the functionalization of the azaborines. This azaborinyl building block can serve as the electrophile in palladium-catalyzed cross-coupling reactions to form sp(3)-sp and sp(3)-sp(2) bonds. The cross-coupling reactions of 2-(chloromethyl)-2,1-borazaronaphthalene with potassium (hetero)aryl- and alkenyltrifluoroborates as well as terminal alkynes provides access to a variety of novel azaborines, allowing a library of pseudobenzylic substituted azaborines to be prepared from one common starting material.
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