Issue 68, 2020
From the journal:

Chemical Communications

Selective strain-promoted azide–alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold†

Keisuke Adachi,a   Tomohiro Meguro,a   Yuki Sakata,a   Kazunobu Igawa, ORCID logo b   Katsuhiko Tomooka, ORCID logo b   Takamitsu Hosoya ORCID logo a  and  Suguru Yoshida ORCID logo *a  

* Corresponding authors

a Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
E-mail: s-yoshida.cb@tmd.ac.jp

b Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka 816-8580, Japan

Abstract

Complexation of bicyclo[6.1.0]nonynes with a cationic silver or gold salt results in protection from a click reaction with azides. The cycloalkyne protection using the silver or gold salt enables selective strain-promoted azide–alkyne cycloadditions of diynes keeping the bicyclo[6.1.0]nonyne moiety unreacted.

Graphical abstract: Selective strain-promoted azide–alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold

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Article information

DOI
https://doi.org/10.1039/D0CC04606J
Article type
Communication
Submitted
03 Jul 2020
Accepted
15 Jul 2020
First published
16 Jul 2020
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2020,56, 9823-9826

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Selective strain-promoted azide–alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold

K. Adachi, T. Meguro, Y. Sakata, K. Igawa, K. Tomooka, T. Hosoya and S. Yoshida, Chem. Commun., 2020, 56, 9823 DOI: 10.1039/D0CC04606J

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