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. 2012 Mar 12;51(11):2667-72.
doi: 10.1002/anie.201108608. Epub 2012 Jan 27.

A general solution for the 2-pyridyl problem

Graham R Dick  1 , Eric M Woerly, Martin D Burke
Affiliations
Free PMC article

A general solution for the 2-pyridyl problem

Graham R Dick et al. Angew Chem Int Ed Engl. .
Free PMC article

Abstract

Problem solved: an air-stable 2-pyridyl borane that can effectively couple to a wide range of aryl and heteroaryl halides and pseudohalides has evaded the synthesis community for decades. The discovery that Cu(DEA)(2) powerfully enables palladium-mediated cross-couplings with air-stable boronates 1 has finally provided a general solution to this problem. DEA=diethanolamine, DMF=N,N'-dimethylformamide, Tf=trifluoromethanesulfonyl.

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Figures

Figure 1
Figure 1
The 2-pyridyl motif is found in many important small molecules.
Scheme 1
Scheme 1
a) 2-pyridyl MIDA boronate 1 a is the first air-stable 2-pyridyl borane that can be isolated in chemically pure form. b) An inexpensive, environmentally friendly, and scalable method for preparing 2-pyridyl MIDA boronates. c) A preliminary method for cross-coupling 1 a with activated aryl chlorides. This method is ineffective with more challenging deactivated aryl halides. dba=dibenzylideneacetone, DMF=N,N′-dimethylfomamide, DMSO=dimethyl sulfoxide, IPA=isopropyl alcohol.
Scheme 2
Scheme 2
Two possible pathways for the DEA-promoted coupling of 1 a.
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
Scheme 6
Scheme 6
See this image and copyright information in PMC

References

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    1. Gillis EP, Burke MD. J. Am. Chem. Soc. 2007;129:6716–6717. - PubMed
    1. Lee SJ, Gray KC, Paek JS, Burke MD. J. Am. Chem. Soc. 2008;130:466–468. - PMC - PubMed
    1. Gillis EP, Burke MD. J. Am. Chem. Soc. 2008;130:14084–14085. - PMC - PubMed
    1. Woerly EM, Cherney AH, Davis EK, Burke MD. J. Am. Chem. Soc. 2010;132:6941–6943. - PMC - PubMed

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