Synthesis of 1,2‐Naphthalenediol Diacetates by Rhodium(II)‐Catalyzed Reaction of 1,2‐Diazonaphthoquinones with Acetic Anhydride

Abstract

A metal-catalyzed reaction of α-diazocarbonyl compounds with an acid anhydride is reported. In particular, 1,2-naphthalenediol diacetates were synthesized by the reaction of 1,2-

Hypervalent Iodine-Mediated Diastereoselective α-Acetoxylation of Cyclic Ketones

“…Therefore, considerable efforts have been made in the development of synthetic protocols for α-acetoxylation of ketones ( Scheme 1 ). Traditional methods to prepare α-acetoxy ketones are the acetolysis of α-diazo ketone (Newman and Beal, 1950 ; Erickson et al, 1951 ; Corey and Knapp, 1976 ; Kitamura et al, 2012 ; Wang et al, 2014 ; Tan et al, 2016 ; Yuan et al, 2016 ; Zhang et al, 2016 ; Hu et al, 2018 ), α-bromo ketone (Tanner et al, 1991 ; Valgimigli et al, 2003 ; Ahmed and Langer, 2006 ; Chen et al, 2013 , 2016 ; Nolla-Saltiel et al, 2014 ; Carneiro et al, 2015 ; Liu et al, 2016 ; Yuan et al, 2019 ), and in situ generated α-iodo derivatives (Du et al, 2015 ; Ren et al, 2016 ; Chen et al, 2017 ; Tan et al, 2017 ; Pogaku et al, 2019 ), which usually require the pre-functionalization of ketones ( Scheme 1A ). In contrast, umpolung reactions have taken a prominent place for the direct α-oxygenation of carbonyl compounds via oxidation of the enolates or related derivatives with transition metal complexes (Littler, 1962 ; Heiba and Dessau, 1971 ; Ng and Henry, 1976 ; Rubottom et al, 1983 ; El-Qisairi and Qaseer, 2002 ; Hamed et al, 2012 ), or hypervalent iodine reagents (Mizukami et al, 1978 ; Nicolaou et al, 2002 ; Bogevig et al, 2004 ; Sunden et al, 2004 ; Ochiai et al, 2005 ; Huang et al, 2007 ; Yu et al, 2010 ; Izquierdo et al, 2016 ; Arava et al, 2017 ) ( Scheme 1B ).…”

Donor–Acceptor–Acceptor 1,3-Bisdiazo Compounds: An Exploration of Synthesis and Stepwise Reactivity

“…Known reactivity of these early systems is largely limited to their decomposition by metal salts, heat, or light, often proceeding through either Wolff rearrangements or cyclopropenone formation (Figure b). ,,,, Selective metal-catalyzed bond forming reactions of 1,3-bisdiazo compounds are rare in the literature. , With respect to order of reaction, it was known that tethered bisdiazo compounds react in a predictable manner, with more rapid decomposition of the donor–acceptor diazo, for the reasons discussed above. − However, what was known about the order of reactivity in these 1,3-bidiazo settings was largely limited to a wavelength dependent product distribution reported by Murata and Tomioka. , …”