A Metal-Free Path to 2-Iodo-3-alkyl-1-arylbut-2-en-1-ones and Their Application to the Domino Synthesis of Functionalized 2H-Pyran-2-ones

Sreenivasulu, Chinnabattigalla and Satyanarayana, G (2022) A Metal-Free Path to 2-Iodo-3-alkyl-1-arylbut-2-en-1-ones and Their Application to the Domino Synthesis of Functionalized 2H-Pyran-2-ones. The Journal of Organic Chemistry, 87 (5). pp. 2222-2240. ISSN 0022-3263

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Abstract

We report a metal-free selective synthesis of 2-iodo-3-alkyl-1-arylbut-2-en-1-ones from propargylic alcohols that is enabled by N-iodosuccinimide. A variety of substituted propargylic alcohols are amenable to delivering the selective 2-iodoenone products in very good yields. The utility of the α-iodoenone derivatives is further extended by developing an efficient, novel, and new synthetic methodology for the synthesis of 3,5,6-trisubstituted 2H-pyran-2-ones. To the best of our knowledge, this protocol is the first of its kind to accomplish 3,5,6-trisubstituted 2H-pyran-2-ones through an unprecedented domino (formation of two C-C bonds and one C-O bond) one-pot process via intermolecular Heck coupling, base-driven Michael addition, and base-mediated double bond isomerization followed by cyclo-condensation. This protocol showed good compatibility with a wide range of iodoenones (18 examples) and 2H-pyran-2-ones (42 examples). Mechanistic studies indicate that palladium is only involved in the Heck coupling; the base solely drives the rest of the steps. © 2022 American Chemical Society. All rights reserved.

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IITH Creators:

IITH Creators	ORCiD
Satyanarayana, G.	UNSPECIFIED

Item Type:

Article

Additional Information:

We greatly acknowledge the financial support from Council of Scientific and Industrial Research ((CSIR), no. 02(0262)/16/EMR-II) and DST-SERB (Department of Science and Technology, Science and Engineering Research Board, Grant EMR/2017/005312), New Delhi. C.B.S thanks UGC New Delhi for providing the fellowship.

Uncontrolled Keywords:

Free path; Functionalized; Heck coupling; Is-enabled; Metal free; N-Iodosuccinimide; Propargylic alcohols; Pyran-2-ones; Selective synthesis; Synthetic methodology

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

22 Jul 2022 06:27

Last Modified:

22 Jul 2022 06:27

URI:

http://raiithold.iith.ac.in/id/eprint/9573