Copper(I)-Mediated Cascade Reactions: An Efficient Approach to the Synthesis of Functionalized Benzofuro[3,2-<i>d</i>]pyrimidines

A novel cascade reaction was developed for the synthesis of diverse members of a series of benzofuro[3,2-<i>d</i>]pyrimidine derivatives. The process utilizes readily prepared 3-chlorochromenones and various commercially available amidines and their analogues as starting materials. This tandem reaction is promoted by using a simple copper(I) reagent and involves a chemoselective Michael addition–heterocyclization–intramolecular cyclization sequence

Supplementary_material – Supplemental material for CD44 overexpression related to lymph node metastasis and poor prognosis of pancreatic cancer

<p>Supplemental material, Supplementary_material for CD44 overexpression related to lymph node metastasis and poor prognosis of pancreatic cancer by Yijuan Liu, Ting Wu, Dong Lu, Jiantao Zhen and Lin Zhang in The International Journal of Biological Markers</p

Cu-Catalyzed Dual C–O Bonds Cleavage of Cyclic Ethers with Carboxylic Acids, NaI, and TMSCF₃ to Give Iodoalkyl Ester

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 TMSCF3. This allows for the concise synthesis of highly functionalized iodoalkyl esters directly. And the synthetic insect pheromones were also disclosed

Cu-Catalyzed Dual C–O Bonds Cleavage of Cyclic Ethers with Carboxylic Acids, NaI, and TMSCF₃ to Give Iodoalkyl Ester

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 TMSCF3. This allows for the concise synthesis of highly functionalized iodoalkyl esters directly. And the synthetic insect pheromones were also disclosed

Copper-Catalyzed Regioselective Iodoformylation of Terminal Alkynes to Access Versatile Electrophiles (<i>E</i>)‑β-Iodo-α,β-Unsaturated Aldehydes

Herein, we describe a method for synthesizing (E)-β-iodo-α,β-unsaturated aldehydes via the iodoformylation of terminal alkynes with TMSCF3 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-iodo-α,β-unsaturated aldehydes with excellent chemoselectivity, regioselectivity, and stereoselectivity. Moreover, it was demonstrated that this protocol has abundant organic reactivity

Copper-Catalyzed Regioselective Olefination and Trifluoromethylation of Carboxylic Acids To Give (<i>Z</i>)‑Trifluoromethyl Enol Esters

Herein, we describe a method to produce (Z)-trifluoromethyl enol esters via the olefination and trifluoromethylation of carboxylic acids with TMSCF3. This synthetic method uses inexpensive and easy-to-handle TMSCF3. It employs a commercially available CuCl catalyst to transform a broad range of carboxylic acids into versatile (Z)-trifluoromethyl enol esters with good regio- and stereoselectivity. This protocol allows the concise synthesis of highly functionalized (Z)-trifluoromethyl enol esters directly from carboxylic acids

Cu-Catalyzed Dual C–O Bonds Cleavage of Cyclic Ethers with Carboxylic Acids, NaI, and TMSCF₃ to Give Iodoalkyl Ester

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 TMSCF3. This allows for the concise synthesis of highly functionalized iodoalkyl esters directly. And the synthetic insect pheromones were also disclosed

Synthesis of (Deoxy)difluoromethylated Phosphines by Reaction of R₂P(O)H with TMSCF₃ and Their Application in Cu(I) Clusters in Sonogashira Coupling

R2PCF2H ligands and their R2P­(O)­CF2H precursors were synthesized from R2P­(O)H with TMSCF3 by simply modulating the H2O concentration via deoxydifluoromethylation and difluoromethylation. The air sensitive R2PCF2H 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

Synthesis of (Deoxy)difluoromethylated Phosphines by Reaction of R₂P(O)H with TMSCF₃ and Their Application in Cu(I) Clusters in Sonogashira Coupling

R2PCF2H ligands and their R2P­(O)­CF2H precursors were synthesized from R2P­(O)H with TMSCF3 by simply modulating the H2O concentration via deoxydifluoromethylation and difluoromethylation. The air sensitive R2PCF2H 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

Nickel-Catalyzed Remote C4–H Arylation of 8‑Aminoquinolines

A useful and convenient method for C–H bond arylation of 8-aminoquinoline motifs on the remote C4 position was developed. This method shows good functional group tolerance toward various Grignard reagents and aminoquinoline via a nickel catalysis, giving the desired arylated products in good yields. The present method affords an efficient access to construct multisubstituted aminoquinolines