Accessing Molecularly Complex Azaborines: Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings of Brominated 2,1-Borazaronaphthalenes and Potassium Organotrifluoroborates

Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki–Miyaura cross-coupling o...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 14; pp. 6663 - 6678
Main Authors Molander, Gary A, Wisniewski, Steven R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.07.2014
Amer Chemical Soc
Subjects
Aza Compounds - chemistry
Borates - chemistry
Boron Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Organometallic Compounds - chemistry
Palladium - chemistry
Physical Sciences
Potassium - chemistry
Science & Technology
EFFICIENT ACCESS
MODULAR APPROACH
B-N
MECHANISM
RESONANCE
ACIDS
C-C
CHEMICAL SPACE
ALKYNES
DERIVATIVES
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Summary:Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki–Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes has been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)­aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)­aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo5011894