Photoinduced group transfer radical addition of carbamotelluroates to acetylenes

Citation
S. Fujiwara et al., Photoinduced group transfer radical addition of carbamotelluroates to acetylenes, ORG LETT, 3(13), 2001, pp. 2085-2088
Citations number
72
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
13
Year of publication
2001
Pages
2085 - 2088
Database
ISI
SICI code
1523-7060(20010628)3:13<2085:PGTRAO>2.0.ZU;2-S
Abstract
[GRAPHICS] Te-Phenyl carbamotelluroates 1 add to acetylenes under irradiation of visib le light to yield beta -telluroacrylamides 2 regioselectively. This reactio n would be initialed by homolytic cleavage of the carbamoyl carbon-telluriu m bond, producing carbamoyl and PhTe radicals, The addition reaction procee ds via a radical chain mechanism comprising two processes: (i) addition of carbamoyl radicals at the terminal carbon of the triple bond, giving vinyli c radicals, and (ii) S(H)2 reaction on the Te atom caused by the attack of the vinyl radicals to 1.