Herein, by dual C−O bond cleavage of cyclic ethers with Cu catalysis, we eventually led to the development of a selective three-component coupling of commercially available chemicals, carboxylic acids, ethers, and halogens to synthesize more than 70 iodoalkyl esters in the presence of TMSCF 3 . This allows for the concise synthesis of highly functionalized iodoalkyl esters directly. And the synthetic insect pheromones were also disclosed.

R 2 PCF 2 H ligands and their R 2 P(O)CF 2 H precursors were synthesized from R 2 P(O)H with TMSCF 3 by simply modulating the H 2 O concentration via deoxydifluoromethylation and difluoromethylation. The air sensitive R 2 PCF 2 H phosphines can be stabilized in Cu(I) clusters as ligands. Within these Cu(I) clusters, the Sonogashira cross-coupling reaction can proceed fast and efficiently using terminal alkynes and aryl iodides within 15 min at room temperature under air to give a variety of diaryl(alkyl)acetylenes in good yields (49 examples, yields of ≤99%). Six of the internal alkynes present in drug precursors can be obtained using this protocol in good yields. The mechanism is proposed on the basis of control experiments.

Herein, we describe a method for synthesizing (E)β-iodo-α,β-unsaturated aldehydes via the iodoformylation of terminal alkynes with TMSCF 3 and NaI. This synthetic method uses inexpensive and easy-to-handle chemical feedstocks and employs a commercially available CuI catalyst. It can transform a broad range of terminal alkynes into bis-electrophile (E)-β-iodoα,β-unsaturated aldehydes with excellent chemoselectivity, regioselectivity, and stereoselectivity. Moreover, it was demonstrated that this protocol has abundant organic reactivity.

Herein, we developed an efficient and transition-metal-free multicomponent coupling reaction for the synthesis of aroyloxyl alkyl iodides. In the reaction among 2,4,6-triarylboroxines, THF, TMSCF3, LiOH, and NaI, five-component reactions could be precisely controlled by modulating CF3SO2Na, supplying one type of aroyloxyl alkyl iodides in moderate to high yields. The reaction exhibits good functional group tolerance and a wide substrate scope and can be easily transformed into other useful compounds. The mechanism is proposed on the basis of the control experiments

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