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Synfacts 2015; 11(1): 0074
DOI: 10.1055/s-0034-1379655
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Accessing 2-(Hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes

Contributor(s):
Paul Knochel
,
Thomas Klatt
Molander GA, * Amani J, Wisniewski SR. University of Pennsylvania, Philadelphia, USA
Accessing 2-(Hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplings of 2-(Chloromethyl)-2,1-borazaronaphthalenes.

Org. Lett. 2014;
16: 6024-6027
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

boron - cross-coupling - borazaronaphthalenes

Significance

The authors expanded the electrophilic nature of 2-(chloromethyl)-2,1-borazaro­naphthalene. In addition to substitution reactions, now also several metal-catalyzed reactions were performed. Potassium (hetero)aryl and alkenyl trifluoroborates as well as terminal alkynes were successfully used as nucleophiles.


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Comment

Impressively, a wide variety of substituted azaborines were prepared starting from one common azaborinyl building block. This new methodology gives access to a whole library of pseudobenzylic-substituted azaborines.


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