2876-53-1Relevant articles and documents
Iron-catalyzed alkylations of aryl sulfamates and carbamates
Silberstein, Amanda L.,Ramgren, Stephen D.,Garg, Neil K.
supporting information; experimental part, p. 3796 - 3799 (2012/08/28)
The alkylation of aryl sulfamates and carbamates using iron catalysis is reported. The method constructs sp2-sp3 carbon-carbon bonds and provides synthetically useful yields across a range of substrates (>35 examples). The directing group ability of sulfamates and carbamates, accompanied by their low reactivity toward conventional cross-couplings, renders these substrates useful for the synthesis of polyfunctionalized arenes.
Activation of C-H bonds of hydrocarbons by the ArH-alkali metal systems in THF (ArH - naphthalene, biphenyl, anthracene, phenanthrene, trans-stilbene, pyrene). Alkylation of naphthalene and toluene with ethene
Rummel,Ilatovskaya,Yunusov,Kalyuzhnaya,Shur
experimental part, p. 1459 - 1466 (2009/09/06)
Systems based on naphthalene and alkali metals (Li, Na, K) in THF are able to induce the alkylation of naphthalene with ethene at room temperature and atmospheric pressure. The highest activity in this reaction is exhibited by the naphthalene-potassium system which converts naphthalene into 1-ethylnaphthalene (1) and small amounts of two isomeric dihydro derivatives of 1 in a yield of 85% (24 h, K:C10H8 = 2:1). The same alkylation products are formed when metallic sodium is used instead of potassium. The interaction of ethene with the naphthalene-lithium system (24 h, Li:C10H8 = 2:1) affords 1 together with 1-n-butylnaphthalene (4), 1-n-hexylnaphthalene (5), 1-n-oktylnaphthalene (6) and dihydro derivatives of 5 and 6 in a total yield of 60%. Alkylation of toluene with ethene in the naphthalene-alkali metal systems leads to the formation of higher monoalkylbenzenes. The greatest toluene conversion (48%, 24 h) is observed on using the lithium-containing system (Li:C10H8 = 2:1), in the presence of which a mixture of n-propylbenzene (11), n-pentylbenzene (12), 3-phenylpentane (13) and 3-phenylheptane (14) is produced from ethene and toluene. On the replacement of lithium by sodium or potassium, only 11 and 13 are obtained. A treatment of biphenyl, phenanthrene, trans-stilbene, pyrene and anthracene with alkali metals in THF also gives systems capable of catalyzing the alkylation of toluene with ethene at 22 °C. Of particularly active is the stilbene-lithium system (Li:stilbene = 3:1) which converts toluene into a mixture of 11-14, n-heptylbenzene and 5-phenylnonane in a yield of 58%. In all cases, the rate of the alkylation considerably increases in the presence of the solid phase of alkali metal. The mechanism of the reactions found is discussed.