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Unexpected Electronic Behavior of Organic Azide and Metal‐Carbyne in Their 1, 3‐Dipolar Cycloaddition Reaction
Author(s) -
Zhang JingXuan,
Sheong Fu Kit,
Lu Zhengyu,
Zhang Hong,
Lin Zhenyang
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000216
Subject(s) - carbyne , chemistry , azide , cycloaddition , regioselectivity , nucleophile , electrophile , 1,3 dipolar cycloaddition , photochemistry , organic chemistry , catalysis , carbene
Summary of main observation and conclusion 1,3‐Dipolar cycloaddition reaction between organic azide and metal carbyne is a useful strategy to construct metallacycles. However, the electronic behavior of organic azide in 1,3‐dipolar cycloaddition reactions is less explored. This work revealed the unexpected role of organic azide as electrophiles in its cycloadditions with various metal carbynes. The feasibility and regioselectivity of a Fischer‐type osmium carbyne in its reaction with an organic azide are explained by the increased nucleophilicity of carbyne carbon upon bending.