Cobalt-Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4-Chromanones

Angewandte Chemie
Junfeng Yang, Naohiko Yoshikai

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 Co(I) catalysis described herein is complementary to the Rh(I) - and Rh(III) -catalyzed reactions of SA and internal alkynes, particularly in the context of chromone synthesis.

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Citations

Apr 26, 2017·The Journal of Organic Chemistry·Robert J SmithBill C Hawkins
Mar 25, 2018·Chemistry : a European Journal·Shintaro YamaneTetsuya Satoh
Oct 28, 2016·Chemical Communications : Chem Comm·Swagata BaruahSanjib Gogoi
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Jan 28, 2020·Organic & Biomolecular Chemistry·Mi-Zhuan LiYong-Zheng Chen
Aug 20, 2020·Chemical Communications : Chem Comm·Se Hun Kwak, Olafs Daugulis
Dec 9, 2020·Chemistry : a European Journal·Lin XiaoGui-Xin Cai
Apr 20, 2021·Chemical Communications : Chem Comm·Shyam Kumar BanjarePonneri Chandrababu Ravikumar
Jul 25, 2019·Organic Letters·Wei DingNaohiko Yoshikai

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