Highly Stereoselective Synthesis of Multisubstituted Olefins from Alkynyl Tetracoordinate Borons and Iodonium Ylides via a Cyclic Intermediate - Details

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Liang, J. (Liang, J..) ^[1] | Chen, X. (Chen, X..) ^[2] | Chen, J. (Chen, J..) ^[3] | Ma, X. (Ma, X..) ^[4] | Song, Q. (Song, Q..) ^[5]

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Abstract：

We　developed　an　intriguing　and　practical　strategy　for　highly　stereoselective　assembly　of　multisubstituted　olefins　from　alkynyl　tetracoordinate　boron　species　via　a　cyclic　intermediate　with　1,2-phenyl　migration.　We　also　developed　a　general　method　for　the　construction　of　deuterated　trisubstituted　alkenes　from　a　cheap　deuteration　source,　D2O,　and　the　corresponding　deuterated　trisubstituted　alkenes　were　obtained　with　excellent　deuteration　rates.　This　transformation　features　a　novel　reaction　mechanism,　exclusive　stereoselectivity,　and　deuterated　trisubstituted　alkenes　with　excellent　deuteration　ratios.　©　2024　American　Chemical　Society.

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[ 1 ] [Liang J.]College of Materials Science and Engineering, Fuzhou University, Fujian, Fuzhou, 350108, China
[ 2 ] [Chen X.]College of Materials Science and Engineering, Fuzhou University, Fujian, Fuzhou, 350108, China
[ 3 ] [Chen J.]College of Materials Science and Engineering, Fuzhou University, Fujian, Fuzhou, 350108, China
[ 4 ] [Ma X.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou, 350108, China
[ 5 ] [Song Q.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou, 350108, China
[ 6 ] [Song Q.]School of Chemistry and Chemical Engineering, Henan Normal University, Henan, Xinxiang, 453007, China
[ 7 ] [Song Q.]State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

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Organic Letters

ISSN： 1523-7060

Year： 2024

Issue： 18

Volume： 26

Page： 3872-3877

4 . 9 0 0

JCR@2023

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