Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/83163
Title: Cobalt-Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4-Chromanones
Authors: Yang, Junfeng
Yoshikai, Naohiko
Keywords: C-H functionalization
Cobalt
Issue Date: 2016
Source: Yang, J., & Yoshikai, N. (2016). Cobalt-Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4-Chromanones. Angewandte Chemie International Edition, 55(8), 2870-2874.
Series/Report no.: Angewandte Chemie International Edition
Abstract: A unique cobalt(I)–diphosphine catalytic system has been identified for the coupling of salicylaldehyde (SA) and an internal alkyne affording a dehydrogenative annulation product (chromone) or a reductive annulation product (4-chromanone) depending on the alkyne substituents. Distinct from related rhodium(I)- and rhodium(III)-catalyzed reactions of SA and alkynes, these annulation reactions feature aldehyde C−H oxidative addition of SA and subsequent hydrometalation of the C=O bond of another SA molecule as common key steps. The reductive annulation to 4-chromanones also involves the action of Zn as a stoichiometric reductant. In addition to these mechanistic features, the CoI catalysis described herein is complementary to the RhI- and RhIII-catalyzed reactions of SA and internal alkynes, particularly in the context of chromone synthesis.
URI: https://hdl.handle.net/10356/83163
http://hdl.handle.net/10220/42480
ISSN: 1433-7851
DOI: 10.1002/anie.201510999
Rights: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Angewandte Chemie International Edition, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/anie.201510999].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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