RESEARCH ARTICLE
Kelly, M. A. Mercadante, N. E. Leadbeater, Chem.
mechanism involving the photolysis of bromodifluor-
oacetamides. Subsequently, the addition of the resul-
tant difluoroalkyl radical species to 1-iodoalkynes is
followed by iodine atom elimination. The synthetic
utility of the coupling products was further demon-
strated by their divergent transformation into various
organofluorine compounds such as trisubstituted
difluoromethylalkenes, 3-fluorofurans, and fused aro-
matic compounds containing a difluoromethylene unit.
De Kimpe, M. D’hooghe, Synlett 2016, 27, 1486–1510;
M. Chaurasia, S. Desai, S. Potkule, S. Sharma, Adv.
[5] Selected reviews: a) S. Arimitsu, G. B. Hammond,
Chimica Oggi/Chemistry Today 2010, 28, 20–22; b) T.
Konno, Synlett 2014, 25, 1350–1370; c) C. Tresse, S.
Schweizer, P. Bisseret, J. Lalevée, G. Evano, N.
Blanchard, Synthesis 2016, 48, 3317–3330; d) A. Ha-
chem, D. Grée, S. Chandrasekhar, R. Grée, Synthesis
2017, 49, 2101–2116; e) J. Escorihurla, D. M. Sedgwick,
A. Liobat, M. Medio-Simón, P. Barrio, S. Fustero,
Beilstein J. Org. Chem. 2020, 16, 1662–1682.
[6] Selected reviews: a) P. Gao, X.-R. Song, X.-Y. liu, Y.-M.
Belhomme, T. Besset, T. Poisson, X. Pannecoucke,
M. R. P. Heravi, A. Ebadi, A. Hosseinian, E. Vessally, J.
Experimental Section
Reaction of 1a with 5a:
A solution of 5a (77.7 mg,
0.318 mmol), iodoalkyne 1a (165 mg, 0.639 mmol), and TME-
DA (90 μL, 0.6 mmol) in degassed MeCN (3 mL) was stirred
under irradiation (LED 448 nm, Techno Sigma PER-AMP) at
room temperature under an Ar atmosphere for 5 h. The reaction
was quenched by adding H2O (20 mL) and sat. aq. Na2S2O3
(5 mL). The aqueous phase was extracted with AcOEt (3×
10 mL). The combined organic extract was washed with brine
(10 mL), dried over anhydrous Na2SO4. The solvents were
evaporated in vacuo, and the obtained crude product was
purified by silica gel column chromatography (hexane/AcOEt
90:1~2:1) to afford 6aa (76.2 mg, 81%) as a colorless solid
[7] Methods using stoichiometric copper reagents: a) O.
Kitagawa, T. Taguchi, Y. Kobayashi, Chem. Lett. 1989,
389–392; b) T. Besset, T. Poisson, X. Pannecoucke, Eur.
°
(mp 77.7–81.8 C).
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c) Y. Xiao, Y.-K. Chun, S.-C. Cheng, R. Liu, M.-K. Tse,
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[12] Selected examples: a) F.-L. Zeng, K. Sun, X.-L. Chen,
X.-Y. yuan, S.-Q. He, Y. Liu, Y.-Y. Peng, L.-B. Qu, Q.-Y.
942–951; c) T. Mao, M.-J. Ma, L. Zhao, D.-P. Xue, Y.
1818; d) L. Helmecke, M. Spittler, B. M. Schmidt, C.
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Acknowledgements
This research is partially supported by the Platform Project for
Supporting Drug Discovery and Life Science Research (Basis
for Supporting Innovative Drug Discovery and Life Science
Research (BINDS) from AMED under Grant Number
JP21am0101099).
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