Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles.
In: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry, Jg. 61 (2020-12-10), Heft 50, S. N.PAG
Online
academicJournal
Zugriff:
• Synthesis of diverse libraries of biaryl-amides from aryl-nitriles. • IL-mediated Ritter reaction followed by Pd-catalyzed directed ortho -arylation. • Use of [BMIM(SO 3 H)][OTf] and tetramethyl guanidinium-ILs [TMG][X] as dual catalysts/solvents. • Feasibility for sequential reaction. Diverse libraries of biaryl-amides bearing N - t -butyl and N -adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO 3 H)][OTf] (neat or with [BMIM][PF 6 as co-solvent) or tetramethyl guanidinium-ILs [TMG][X] (X = CF 3 COO, EtOSO 3) as dual catalyst/solvent, followed by a Pd-catalyzed directed regioselective ortho C H arylation of the Ritter amides with Ar-X (X = I, Cl). The feasibility to perform the two-steps in sequence is also demonstrated, and potential for recycling/reuse of the ILs is also shown. Preference for [Pd] coordination to the amide carbonyl versus amide nitrogen is borne out by DFT computations. [ABSTRACT FROM AUTHOR]
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Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles.
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Autor/in / Beteiligte Person: | Sutar, Suraj M. ; Savanur, Hemantkumar M. ; Kalkhambkar, Rajesh G. ; Borosky, Gabriela L. ; Aridoss, Gopalakrishnan ; Laali, Kenneth K. |
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Zeitschrift: | Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry, Jg. 61 (2020-12-10), Heft 50, S. N.PAG |
Veröffentlichung: | 2020 |
Medientyp: | academicJournal |
ISSN: | 0040-4039 (print) |
DOI: | 10.1016/j.tetlet.2020.152553 |
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