14751-81-6

Upstream product

• 94365-53-4 (PPh₃)(1,10-phenanthroline)Cu(NC(S)SN₂) 
• 98-88-4 benzoyl chloride 
• 603-35-0 triphenylphosphine 
• 66-71-7 1,10-Phenanthroline 
• 874-60-2 4-methyl-benzoyl chloride 
• 933-88-0 ortho-toluoyl chloride 
• 42926-52-3 2-ethoxybenzoyl chloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 393-52-2 2-Fluorobenzoyl chloride 
• 403-43-0 4-fluorobenzoyl chloride 
• 72482-64-5 2,4-difluorobenzoyl chloride 
• 2251-50-5 pentafluorobenzoylchloride 

Relevant academic research and scientific papers

Role of a Copper Complex in an Oxygen-atom Transfer Reaction from Dioxygen to Triphenylphosphine

Unexpectedly, 1,10-phenanthroline-CuICl (phen-CuCl) reacts with dioxygen to give only one oxygenated complex (yield 95percent), the stoicheiometry of which is (phenCuCl)2O; the quantitative transfer of an oxygen atom from this complex to triphenylphosphine is also reported.

Dynamic multiligand catalysis: A polar to radical crossover strategy expands alkyne carboboration to unactivated secondary alkyl halides

We describe a dual strategy in Cu catalysis based on an unprecedented dynamic multiligand coordination pool that triggers cooperative polar/radical pathways in a single catalytic cycle. This strategy has been applied to address a restricting limitation inherent to Cu-catalyzed B2pin2-carboboration of alkynes—the very low reactivity of the intermediate vinyl-Cu(I) species, which renders conventional methods ineffective with alkyl electrophiles other than simple primary halides. The crossover strategy enabled by ligand exchange in an organometallic intermediate overcomes this reactivity issue, expanding the scope of carboboration to unactivated secondary alkyl halides, and opens new avenues to access stereodefined tetrasubstituted vinylboronates. The method is regio- and stereoselective, shows excellent functional group tolerance, and allows the incorporation of complex carbo- and heterocyclic fragments at either reaction partner.

Well-defined CuC2F5 complexes and pentafluoroethylation of acid chlorides

Four new well-defined CuI complexes bearing a C2F5 ligand have been prepared and fully characterized: [(Ph3P)2CuC2F5] (2), [(bpy)CuC2F5] (3), [(Ph3P)Cu(phen)C2F5] (4), and [(IPr)CuC2F5] (5). X-ray structures of all four have been determined, showing that the C2F5-ligated Cu atom can be di- (5), tri- (2 and 3), and tetracoordinate (4). The mixed phen-PPh3 complex 4 is a highly efficient fluoroalkylating agent for a broad variety of acid chlorides. This high-yielding transformation represents the first general method for the synthesis of RCOC2F5 from the corresponding RCOCl. Four well-defined CuC2F5 complexes have been prepared and fully characterized, with [(phen)Cu(PPh3)C2F5] (phen=1,10-phenanthroline) proving to be a remarkably efficient fluoroalkylating agent for a broad variety of acid chlorides (see scheme). The procedure represents the first general method for the one-step conversion of RCOCl into valuable pentafluoroethyl ketones.

THE CHEMICAL BAHAVIOUR OF THE AZIDO GROUP BONDED TO COPPER(I): SYNTHESIS AND REACTIVITY OF THIOTHIATRIAZOLATO AND ALKYNYL COMPLEXES

The copper(I) azido-derivatives, (PPh3)(phen)CuN3 (Ia) and (PPh3)(TMP)CuN3 (Ib) (phen = 1,10-phenanthroline; TMP = 3,4,7,8-tetramethyl-1,10-phenanthroline), obtained from 2 and the bidentate ligand (biL), react with CS2 to give the thiothiatriazolato-copper(I) complexes, (IIa) and (IIb).The preparation of IIa and IIb occurs only when free triphenylphosphine is present in the reaction medium.The isothiocyanate complexes, (PPH3)(biL)Cu(NCS) (biL = phen, IIIa; biL = TMP, IIIb) are formed, instead of IIa and IIb, when free PPh3 is not added to the reaction medium.The complexes IIIa and IIIb are also obtained when CH2Cl2 solutions of IIa and IIb are stirred for 15 h in the absence of light; if longer reaction times are used, the dimeric isothiocyanato complexes 2 are formed.Compounds IIa and IIb react with PhCOCl to give (PPh3)(BiL)CuCl and 4-benzoyl-1,2,3,4-thiatriazole-5-thione, .Treatment of Ia and Ib, or 2, with COS did not lead to isolation of characterizable products.An unsaturated molecule such as ethyl propriolate, EtO2CCCH, does not behave as a 1,3-dipolarophile in its reactions with Ia and Ib, the alkynyl derivatives C-CO2Et)2>n (n is probably 2; biL = phen, IVa; biL = TMP, IVb), being obtained.Similarly the azido-complex 2 reacts with ethyl propiolate to give the asymmetric binuclear alkynyl derivative, (PPh3)3Cu2(CC-CO2Et)2 (V).The reaction of V with hydrogen chloride gives EtO2C-CCH and the known complex (PPh3)3Cu2Cl2, confirming the above formulation.The reactions of V with neutral ligands such as TMP, phen and CyNC have also been studied, leading to the isolation of new copper(I) alkynyl-derivatives.