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Molecules 2019, 24, x FOR PEER REVIEW 15 of 42 Molecules 2019, 24, 182 15 of 41 strategy to incorporate CO2 into heterocycles bearing a quaternary carbon center (Scheme 14a). As shown in Scheme 14c, the carboxylation of amine with CO2 and the trans-oxopalladation of C≡C II II Cbo≡nCdboynAdrbPydAXrPsdpeXciespsesceiqeusesneqtiuaelnotciaculorctcouarftforadffoinrdteirnmterdmiaetdeiaAte. SAu.bSsuebqsueeqnutelyn,tliyn,tienrtmeremdieadteiatAe Aunudnedrgeorgeoseasnanrerdeudcuticvtieveleimliminiantaiotino,nd,edperportotnoantaiotinonanadndrereaarrarnanggememenentststotoggeenneerraatetettheeproduct.. Moreover, palladium-catalyzed cyclization reactions of O-haloanilines, CO2 and isocyanides were 2 employed to prepare N3-substituted quinazoline-2,4(1H,3H)-dione with moderate to excellent yields (Scheme 14b) [85]. Scheme 14. Multicomponent reactions including CO2 to synthesize quinazoline-2,4(1H,3H)-diones. Scheme 14. Multicomponent reactions including CO2 to synthesize quinazoline-2,4(1H,3H)-diones. 2.4. Urea Derivatives from Amine Derivatives and CO2 2.4. Urea Derivatives from Amine Derivatives and CO2 It is well known that urea derivatives have a wide range of applications in pharmaceutical It is well known that urea derivatives have a wide range of applications in pharmaceutical chemistry, organic synthesis as well as analytical chemistry [86,87]. Traditionally, urea derivatives chemistry, organic synthesis as well as analytical chemistry [86,87]. Traditionally, urea derivatives were synthesized by the stoichiometric reaction of amines and isocyanates [88]. Moreover, the reaction were synthesized by the stoichiometric reaction of amines and isocyanates [88]. Moreover, the of amines and highly toxic phosgene/phosgene analogs was performed to afford urea derivatives [89]. reaction of amines and highly toxic phosgene/phosgene analogs was performed to afford urea Besides, catalytic oxidative carbonylation of amines in the presence of CO was also developed to derivatives [89]. Besides, catalytic oxidative carbonylation of amines in the presence of CO was also obtain ureas [90]. Notably, alternative synthetic routes of CO2 as a source with amines have attracted developed to obtain ureas [90]. Notably, alternative synthetic routes of CO2 as a source with amines considerable attention in recent years. have attracted considerable attention in recent years. In the last decades, bicyclic guanidines, as important organic bases, have shown to be active In the last decades, bicyclic guanidines, as important′ organic bases, have shown to be active catalysts in chemical fixation of CO2. For example, N,N -dialkylureas were synthesized via the catalysts in chemical fixation of CO2. For example, N,N′-dialkylureas were synthesized via the carbonylation of amines with CO2 using TBD as catalyst (Scheme 15) [91]. Among three TBD-CO2 carbonylation of amines with CO2 using TBD as catalyst (Scheme 15) [91]. Among three TBD-CO2 species (a–c) shown in Scheme 15, the formation of bicarbonate-guanidinium salt c is ascribed to trace species (a–c) shown in Scheme 15, the formation of bicarbonate-guanidinium salt c is ascribed to of water. The reaction proceeds with a sequential electrophilic attack of amine on c, elimination of water from M1 and reaction between M2 and amine leading to N,N′-dialkylureas.PDF Image | Catalytic Conversion of Carbon Dioxide through C-N Bond
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