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Munoz SB, Aloia AN, Moore AK, et al. Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions. Org Biomol Chem. 2015;14(1):85-92doi: 10.1039/c5ob02187a.
Munoz, S. B., Aloia, A. N., Moore, A. K., Papp, A., Mathew, T., Fustero, S., Olah, G. A., & Prakash, G. K. (2016). Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions. Organic & biomolecular chemistry, 14(1), 85-92. https://doi.org/10.1039/c5ob02187a
Munoz, Socrates B, et al. "Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions." Organic & biomolecular chemistry vol. 14,1 (2016): 85-92. doi: https://doi.org/10.1039/c5ob02187a
Munoz SB, Aloia AN, Moore AK, Papp A, Mathew T, Fustero S, Olah GA, Prakash GK. Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions. Org Biomol Chem. 2016 Jan 07;14(1):85-92. doi: 10.1039/c5ob02187a. Epub 2015 Nov 27. PMID: 26611810.
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Org Biomol Chem. 2016 Jan 07;14(1):85-92. doi: 10.1039/c5ob02187a. Epub 2015 Nov 27.

Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions.

Organic & biomolecular chemistry

Socrates B Munoz, Alexandra N Aloia, Alexander K Moore, Attila Papp, Thomas Mathew, Santos Fustero, George A Olah, G K Surya Prakash

Affiliations

  1. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA-90089-1661, USA. [email protected].

PMID: 26611810 DOI: 10.1039/c5ob02187a

Abstract

A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl)alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently "unmasked" upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene (TMSA) as a convenient acetylene surrogate was also shown to be feasible under Pd/Cu catalysis.

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