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Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: inoue@mol.f.u-tokyo.ac.jp
; Fax: (+81) 3-5841-0568
Org. Biomol. Chem., 2013,11, 164-169
DOI:
10.1039/C2OB26785C
Received
11 Sep 2012,
Accepted
12 Oct 2012
First published online
16 Oct 2012
A general strategy for photochemical alkynylation of unreactive C(sp3)–H bonds has been developed. After C–H abstraction by the photo-excited benzophenone, a two-carbon unit was efficiently transferred to the generated radical from 1-tosyl-2-(trimethylsilyl)acetylene to afford the alkynylated product. The present reaction enables construction of various tri- and tetra-substituted carbons from heteroatom-substituted methylenes, methines and alkanes in a highly chemoselective fashion, and would serve as a new synthetic strategy for rapid construction of complex structures.
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Organic & Biomolecular Chemistry
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