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Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitriles: efficient synthesis of (Z)-β-sulfonylvinylamines and β-keto sulfones.
Org Lett. 2011 Jan 21; 13(2):208-11.OL

Abstract

An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Tsui GC
Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5H 3H6.
Glenadel Q
No affiliation info available
Lau C
No affiliation info available
Lautens M
No affiliation info available

MeSH

AcetonitrilesBoronic AcidsCatalysisCombinatorial Chemistry TechniquesMolecular StructureRhodiumStereoisomerismSulfones

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21142088

Citation

Tsui, Gavin Chit, et al. "Rhodium(I)-catalyzed Addition of Arylboronic Acids to (benzyl-/arylsulfonyl)acetonitriles: Efficient Synthesis of (Z)-β-sulfonylvinylamines and Β-keto Sulfones." Organic Letters, vol. 13, no. 2, 2011, pp. 208-11.
Tsui GC, Glenadel Q, Lau C, et al. Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitriles: efficient synthesis of (Z)-β-sulfonylvinylamines and β-keto sulfones. Org Lett. 2011;13(2):208-11.
Tsui, G. C., Glenadel, Q., Lau, C., & Lautens, M. (2011). Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitriles: efficient synthesis of (Z)-β-sulfonylvinylamines and β-keto sulfones. Organic Letters, 13(2), 208-11. https://doi.org/10.1021/ol102598p
Tsui GC, et al. Rhodium(I)-catalyzed Addition of Arylboronic Acids to (benzyl-/arylsulfonyl)acetonitriles: Efficient Synthesis of (Z)-β-sulfonylvinylamines and Β-keto Sulfones. Org Lett. 2011 Jan 21;13(2):208-11. PubMed PMID: 21142088.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitriles: efficient synthesis of (Z)-β-sulfonylvinylamines and β-keto sulfones. AU - Tsui,Gavin Chit, AU - Glenadel,Quentin, AU - Lau,Chan, AU - Lautens,Mark, Y1 - 2010/12/13/ PY - 2010/12/15/entrez PY - 2010/12/15/pubmed PY - 2011/3/3/medline SP - 208 EP - 11 JF - Organic letters JO - Org Lett VL - 13 IS - 2 N2 - An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21142088/Rhodium_I__catalyzed_addition_of_arylboronic_acids_to__benzyl_/arylsulfonyl_acetonitriles:_efficient_synthesis_of__Z__β_sulfonylvinylamines_and_β_keto_sulfones_ L2 - https://doi.org/10.1021/ol102598p DB - PRIME DP - Unbound Medicine ER -