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

Paul Knochel; Thomas Klatt

doi:10.1055/s-0034-1379655

Synfacts, Table of Contents

Synfacts 2015; 11(1): 0074
DOI: 10.1055/s-0034-1379655

Metal-Mediated Synthesis

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

Authors

Paul Knochel
Thomas Klatt

Abstract

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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

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.

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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