Journal
ORGANIC LETTERS
Volume 17, Issue 22, Pages 5594-5597Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02741
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Funding
- Natural Science and Engineering Research Council (NSERC)
- Ontario Institute for Cancer Research
- Government of Ontario
- NSERC
- Canadian Foundation for Innovation [19119]
- Ontario Research Fund
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Herein, we describe the bromomethyl acyl boronate linchpin-an enabling reagent for the condensation-driven assembly of novel bis(heteroaryl) motifs. This building block is readily accessible from commercially available starting materials. A variety of 2-amino- and 2-methylpyridines were reacted with MIDA-protected bromomethyl acylboronate to afford 2-boryl imidazo[1,2-a]pyridine and 2-boryl indolizine derivatives, respectively, in excellent yields. Subsequent condensation with hydroxyamidines and hydrazonamides converted the intermediate heterocycles into novel boron-containing bis(heteroaryl) units characterized by high thermal stability.
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