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Title: Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester
Authors: Tan, Ploypailin Siew Ling
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2021
Publisher: Nanyang Technological University
Source: Tan, P. S. L. (2021). Regio- and stereoselective alkyne difunctionalization by using benziodoxole triflate and phosphate ester. Master's thesis, Nanyang Technological University, Singapore.
Abstract: Stereoselective synthesis of tetrasubstituted alkenes has been one of the most challenging subjects in synthetic organic chemistry. Regio- and stereoselective difunctionalization of readily available alkynes represents a conceptually straightforward approach toward this goal. In this Masters study, I have developed such an alkyne difunctionalization reaction using a hypervalent iodine reagent as an electrophile and a phosphate ester as a nucleophile. Thus, a three-component reaction involving an internal alkyne, benziodoxole triflate (BXT), and triethyl phosphate or related phosphate ester proceeds smoothly at room temperature, resulting in trans-addition of the benziodoxole (BX) and phosphate groups. The reaction has proved applicable to a variety of symmetrical and unsymmetrical internal alkynes, thus affording the corresponding β-λ3-iodanyl alkenyl phosphates in a regio- and stereoselective fashion. The BX and phosphate groups of the product can be utilized for sequential cross-coupling, thus allowing for the stereoselective synthesis of all-carbon tetrasubstituted alkenes.
DOI: 10.32657/10356/150700
Rights: This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0).
Fulltext Permission: embargo_20220527
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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