A Lewis acid‐catalyzed formal [3+3] cascade annulation strategy for the formation of diverse tricyclic compounds possessing functionalized pyrano[3,2‐c]chromen‐5(2
A Brønsted acid‐mediated formal [3+3] cascade annulation of propargylic alcohols with 1,3‐diketones proceeds through a sequential Meyer−Schuster rearrangement/1,2‐addition. This protocol, which has a wide scope and is conducted under an ambient atmosphere, enables access to a broad array of valuable chromenone derivatives related to many natural products in satisfactory yields under mild conditions. This method could be scaled up to the gram scale, which highlights the latent applicability of this transformation.
- NSF-PAR ID:
- 10048323
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Advanced Synthesis & Catalysis
- Volume:
- 360
- Issue:
- 5
- ISSN:
- 1615-4150
- Page Range / eLocation ID:
- p. 870-874
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
Abstract H )‐one fragments has been developed using propargylic alcohols and 4‐hydroxy‐2H ‐chromen‐2‐ones as the substrates. The protocol provides a one‐step, environmentally benign method of accessing a broad range of pyrano[3,2‐c]chromen‐5(2H )‐one derivatives in excellent yields under mild conditions and with good functional‐group tolerance. The method is effective on the gram scale, which highlights the inherent practicality of this synthetic transformation.magnified image -
Abstract Diverse alkenylboronic acids react smoothly with various
sp 3‐carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal‐free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling.magnified image -
Abstract A straightforward method for the palladium‐catalyzed triarylation of heteroarylmethanes at the methyl group has been developed. The reaction works with a variety of aryl halides, enabling the rapid synthesis of triaryl(heteroaryl)methanes in moderate to excellent yields.
magnified image -
Abstract Aiming at the enhanced catalytic activity of fluoro‐λ3‐iodane generated from iodoarene precatalyst with Selectfluor and HF⋅pyridine, this study focused on the λ3‐iodanes bearing coordinating substituents. Compared to 4‐iodoanisole as a precatalyst of our previous method,
N ‐methyl‐2‐iodobenzamide or 2‐iodobenzamide worked well in the fluorocyclization ofN ‐propargyl carboxamides to oxazoles. Control experiments suggest the equilibrium mixture of iodane‐amine complexes and cyclic iodane fluorides would be involved in the present catalysis.magnified image -
Abstract We report the synthesis of α‐trifluoromethylacrylates from α‐trifluoroborylacrylates
via a stereoretentive radical trifluoromethylation with inexpensive reagents NaSO2CF3and TBHP at room temperature. Under these conditions, a wide substrate scope afforded the (E )‐diastereomer exclusively in moderate to good yield. The utility of the reaction products is demonstrated in the synthesis of phenyl‐4H ‐pyran, a potent and selective class of IKCa channel blockers.magnified image