Indolines are important moieties present in various biologically significant molecules and have attracted considerable attention in synthetic chemistry. This paper describes a Heck reaction/C-H activation/amination sequence for forming indolines using di-tert-butyldiaziridinone. The reaction process likely proceeds via a pallada(II)cycle, which is converted into an indoline by oxidative addition to the diaziridinone and two subsequent C-N bond formations.
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http://dx.doi.org/10.1002/anie.201405365 | DOI Listing |
Chem Sci
July 2018
Platov South-Russian State Polytechnic University (NPI), Prosveschenya 132 , Novocherkassk , 346428 , Russia.
Numerous reactions are catalyzed by complexes of metals (M) with N-heterocyclic carbene (NHC) ligands, typically in the presence of oxygen bases, which significantly shape the performance. It is generally accepted that bases are required for either substrate activation (exemplified by transmetallation in the Suzuki cross-coupling), or HX capture ( in a variety of C-C and C-heteroatom couplings, the Heck reaction, C-H functionalization, heterocyclizations, ). This study gives insights into the behavior of M(ii)/NHC (M = Pd, Pt, Ni) complexes in solution under the action of bases conventionally engaged in catalysis (KOH, NaOH, -BuOK, CsCO, KCO, ).
View Article and Find Full Text PDFChem Commun (Camb)
January 2015
School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran.
A Catellani reaction terminated by palladacycle amination leading to methanocarbazoles is reported. The outcome is the formation of three different Csp(3)-Csp(2)/Csp(3)-N/Csp(2)-N bonds through a Heck reaction/C-H activation/double amination cascade in one process.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2014
Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA).
Indolines are important moieties present in various biologically significant molecules and have attracted considerable attention in synthetic chemistry. This paper describes a Heck reaction/C-H activation/amination sequence for forming indolines using di-tert-butyldiaziridinone. The reaction process likely proceeds via a pallada(II)cycle, which is converted into an indoline by oxidative addition to the diaziridinone and two subsequent C-N bond formations.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2008
Department of Process Research, Merck Research Laboratories, Merck & Co., Inc. P.O. Box 2000, Rahway, NJ 07065, USA.
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