Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2007 Jan 31;129(4):790-3.
doi: 10.1021/ja064948q.

Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

J R Falck  1 , Paresh K Patel, Anish Bandyopadhyay
Affiliations

Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

J R Falck et al. J Am Chem Soc. .

Abstract

Racemic and scalemic PTC-protected alpha-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl- and stannyl-substituted stereocenters.

PubMed Disclaimer

References

    1. Review: Mitchell TN. Chapter 3 In: de Meijere A, Diederich F, editors. Metal-Catalyzed Cross-Coupling Reactions. 2. Vol. 1. Wiley-VCH Verlag GmbH & Co; Weinheim: 2004.

    1. Recent applications in natural products total synthesis: Nicolaou KC, Koftis TV, Vyskocil S, Petrovic G, Tang W, Frederick MO, Chen DYK, Li Y, Ling T, Yamada YMA. J Am Chem Soc. 2006;128:2859–2872.Snyder SA, Corey EJ. J Am Chem Soc. 2006;128:740–742.Schnermann MJ, Boger DL. J Am Chem Soc. 2005;127:15704–15705.

    1. Bhatt RK, Shin DS, Falck JR, Mioskowski C. Tetrahedron Lett. 1992;33:4885–4888.
    2. Belosludtsev YY, Bhatt RK, Falck JR. Tetrahedron Lett. 1995;36:5881–5882.
    3. Falck JR, Bhatt RK, Reddy KM, Ye J. Synlett. 1997:481–482.
    1. Linderman RJ, Graves DM, Kwochka WR, Ghannam AF, Anklekar TV. J Am Chem Soc. 1990;112:7438–7439.
    1. Ye J, Bhatt RK, Falck JR. J Am Chem Soc. 1994;116:1–5.

Publication types

MeSH terms