Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Organosilanes by Donor/Acceptor Carbenes Derived from Aryldiazoacetates

• Type of Material: Article
• Authors: Zachary J. Garlets, Emory University; Elliot F. Hicks, Emory University; Jiantao Fu, Emory University; Eric A. Voight, AbbVie; Huw Davies, Emory University
• Language: English
• Date: 2019-06-21
• Publisher: AMER CHEMICAL SOC
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2019 American Chemical Society
• Final Published Version (URL): http://dx.doi.org/10.1021/acs.orglett.9b01833
• Title of Journal or Parent Work: ORGANIC LETTERS
• Volume: 21
• Issue: 12
• Start Page: 4910
• End Page: 4914
• Grant/Funding Information: Financial support was provided by AbbVie, NSF under the CCI Center for Selective C-H Functionalization (CHE-1700982) and the NIH (GM099142-05). Z. J. G. was supported on a fellowship from the NIH (F32GM130020). Instrumentation used in this work was supported by the National Science Foundation (CHE 1531620 and CHE 1626172). We wish to thank the members of the NSF Center for C-H Functionalization (CHE-1700982) for helpful discussions regarding this work.
• Keywords: Chemistry; Physical Sciences; BONDS; PRODUCTS; Chemistry, Organic; Science & Technology; INSERTION; MEDICINAL CHEMISTRY; PHENYL(BROMODICHLOROMETHYL)MERCURY-DERIVED DICHLOROCARBENE

Abstract

The regioselective and enantioselective intermolecular sp3 C-H functionalization of silicon-substituted alkanes with aryl diazoacetates was accomplished using the recently developed dirhodium catalyst Rh2(S-TPPTTL)4. These reactions generate a diverse array of stereodefined substituted silacycloalkanes with high enantioselectivity and diastereoselectivity.