Controlled Trifluoromethylation Reactions of Alkynes through Visible‐Light Photoredox Catalysis

Angewandte Chemie - International Edition - Tập 53 Số 2 - Trang 539-542 - 2014
Naeem Iqbal1, Jae Hun Jung2, Sehyun Park2, Eun Jin Cho2,1
1Department of Chemistry and Applied Chemistry, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Kyeonggi-do 426-791, Republic of Korea
2Department of Bionanotechnology, Hanyang University (Republic of Korea)

Tóm tắt

AbstractThe control of a reaction that can form multiple products is a highly attractive and challenging concept in synthetic chemistry. A set of valuable CF3‐containing molecules, namely trifluoromethylated alkenyl iodides, alkenes, and alkynes, were selectively generated from alkynes and CF3I by environmentally benign and efficient visible‐light photoredox catalysis. Subtle differences in the combination of catalyst, base, and solvent enabled the control of reactivity and selectivity for the reaction between an alkyne and CF3I.

Từ khóa


Tài liệu tham khảo

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Isolated2 a(Scheme 1) was subjected to the conditions described in Scheme 2. See the Supporting Information Scheme S1.

Alkenyl iodide 2 awas detected during the reaction of1 a see the Supporting Information Figure S1 (kinetic studies of the reaction with1 a).

It is likely that the reaction proceeded through an alkynyl iodide as the intermediate. For experimental details see the Supporting Information Scheme S2. A plausible mechanism for the trifluoromethylation of alkynes is proposed in Figure S2.