18499-57-5

Upstream product

• 10486-08-5 sodium p-thiocresolate 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 951165-87-0 (9s,10s)-9,10-diethynyl-9,10-dihydroanthracene-9,10-diol 

Downstream Products

• 18499-65-5 1,1-diphenyl-3-(10-phenylbutadiynyl-[9]anthryl)-prop-2-yn-1-ol 
• 18522-43-5 9-ethynyl-10-phenylbutadiynyl-anthracene 

Relevant academic research and scientific papers

Alkyl cyanoferrates, cyanocobaltates, and cyanonickelates as new reagents for cross-coupling with organic halides

Cyano ate-complexes of unknown structure (the following formulae are based only on the stoichiometry of the educts) are produced in situ by the action of 1-4 equivalents of methyllithium on M(CN)2 (where M = Fe, Co, Ni) at -78°C. Some of these new reagents are very favorable to cross-coupling with organic halides: coupling with 1-bromononane can be achieved by Me3Ni(CN)2Li3, Me4Ni(CN)2Li4, or Me4Fe(CN)2Li4 in 83-90% yield, and with 1-chlorononane by Me4Ni(CN)2Li4 in 80% yield. Me2Fe(CN)2Li2 and Me3Fe(CN)2Li3 couple with α-bromostyrene with similar yields (89 and 84%, respectively) as the homoleptic complexes Me4FeLi2 and Me4CoLi2, whereas Me2Co(CN)2Li2 and Me3Co(CN)2Li3 are clearly superior to these complexes in their coupling with 1-bromonaphthalene (giving 89 and 95% yield, respectively). Me3Co(CN)2Li3 and Me4Co(CN)2Li4 gave coupling products with 1-chloro- and 1-fluoronaphthalene in 77 and 67% yield, respectively. MeCo(CN)2Li is by far superior to other stoichiometric reagents in the coupling (81%) with 1-bromo-2-phenylethyne. Butyl cyano ate-complexes cause the cross-coupling on 1-bromononane and 1-bromonaphthalene in unsatisfactory yields due to side reactions.