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Published May 3, 2013 | Version Supplemental Material
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Transition-Metal-Catalyzed Alkylations of Amines with Alkyl Halides: Photoinduced, Copper-Catalyzed Couplings of Carbazoles

Creators

  • 1. ROR icon California Institute of Technology

Abstract

N-alkylations of carbazoles with a variety of secondary and hindered primary alkyl iodides can be achieved by using a simple precatalyst (CuI) under mild conditions (0 °C) in the presence of a Brønsted base; at higher temperature (30 °C), secondary alkyl bromides also serve as suitable coupling partners. A Li[Cu(carbazolide)_2] complex has been crystallographically characterized, and it may serve as an intermediate in the catalytic cycle.

Additional Information

© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 11, 2013; Published online: April 8, 2013. This work was supported by the Gordon and Betty Moore Foundation (grant to J.C.P.), the National Science Foundation (fellowship support for S.E.C.), and the Natural Sciences and Engineering Research Council of Canada (fellowship support for R.J.L.). Assistance with X-ray crystallography from Larry M. Henling is gratefully acknowledged.

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Additional details

Identifiers

Eprint ID
39006
DOI
10.1002/anie.201301202
Resolver ID
CaltechAUTHORS:20130620-145951306

Funding

Gordon and Betty Moore Foundation
NSF
Natural Sciences and Engineering Research Council of Canada (NSERC)

Dates

Created
2013-06-21
Created from EPrint's datestamp field
Updated
2021-11-09
Created from EPrint's last_modified field