Iridium(III)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate

N. Mace Weldy; A. G. Schafer; C. P. Owens; C. J. Herting; A. Varela-Alvarez; S. Chen; Z. Niemeyer; D. G. Musaev; M. S. Sigman; H. M. L. Davies; S. B. Blakey

doi:10.1039/C6SC00190D

Iridium(iii)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate†

N. Mace Weldy,^a A. G. Schafer,^a C. P. Owens,^a C. J. Herting,^a A. Varela-Alvarez,^b S. Chen,^b Z. Niemeyer,^c D. G. Musaev,*^b M. S. Sigman,*^c H. M. L. Davies*^a and S. B. Blakey*^a

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* Corresponding authors

^a Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA
E-mail: sblakey@emory.edu

^b Emerson Center for Scientific Computation, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA

^c Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA

Abstract

The intermolecular enantioselective C–H functionalization with acceptor-only metallocarbenes is reported using a new family of Ir(III)-bis(imidazolinyl)phenyl catalysts, developed based on the interplay of experimental and computational insights. The reaction is tolerant of a variety of diazoacetate precursors and is found to be heavily influenced by the steric and electronic properties of the substrate. Phthalan and dihydrofuran derivatives are functionalized in good yields and excellent enantioselectivities.

Chemical Science

Iridium(iii)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate†

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Iridium(III)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate

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