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Regio- and Stereoselective Rhodium(II)-Catalyzed C–H Functionalization of Cyclobutanes

115 Pages Posted: 16 Sep 2019 Sneak Peek Status: Review Complete

See all articles by Zachary J. Garlets

Zachary J. Garlets

Emory University - Department of Chemistry

Benjamin D. Wertz

Emory University - Department of Chemistry

Wenbin Liu

Emory University - Department of Chemistry

Voight A. Eric

AbbVie - Research and Development

Huw M. L. Davies

Emory University - Department of Chemistry

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Abstract

Recent developments in controlled C–H functionalization transformations continue to inspire new retrosynthetic disconnections. One tactic in C–H functionalization is the intermolecular C–H insertion reaction of rhodium bound carbenes. These intermediates can undergo highly selective transformations through the modulation of the ligand framework of the rhodium catalyst. This work describes our continued efforts towards differentiating C–H bonds in the same molecule by judicious catalyst choice. Substituted cyclobutanes which exist as a mixture of interconverting conformers and possess neighboring C–H bonds within a highly strained framework are the targets herein for challenging the current suite of catalysts. While most C–H functionalization tactics focus on generating 1,2-disubstituted cyclobutanes via substrate-controlled directing group methods, the regiodivergent methods in this paper provide access to chiral 1,1-disubstituted and cis -1,3-disubstituted cyclobutanes simply by changing the catalyst identity, thus permitting entry to novel chemical space.

Keywords: Asymmetric, rhodium, cyclobutanes, diazo compound, C-H functionalization

Suggested Citation

Garlets, Zachary J. and Wertz, Benjamin D. and Liu, Wenbin and Eric, Voight A. and Davies, Huw M. L., Regio- and Stereoselective Rhodium(II)-Catalyzed C–H Functionalization of Cyclobutanes (September 12, 2019). CHEMJOURNAL-D-19-00951. Available at SSRN: https://ssrn.com/abstract=3452782 or http://dx.doi.org/10.2139/ssrn.3452782
This is a paper under consideration at Cell Press and has not been peer-reviewed.

Zachary J. Garlets

Emory University - Department of Chemistry ( email )

United States

Benjamin D. Wertz

Emory University - Department of Chemistry

United States

Wenbin Liu (Contact Author)

Emory University - Department of Chemistry

United States

Voight A. Eric

AbbVie - Research and Development ( email )

United States

Huw M. L. Davies

Emory University - Department of Chemistry ( email )

United States

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