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Recent advances of versatile reagents as controllable building blocks in organic synthesis
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作者 Shaomin Chen luigi vaccaro Yanlong Gu 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第2期24-43,共20页
Diversity-oriented synthesis is a powerful and interesting synthetic tool for the rapid construction of structurally complex and privileged scaffolds from readily accessible starting materials.To date,diversity-orient... Diversity-oriented synthesis is a powerful and interesting synthetic tool for the rapid construction of structurally complex and privileged scaffolds from readily accessible starting materials.To date,diversity-oriented synthesis mostly relies on the employment of versatile reagents.Versatile reagents can be regulated as controllable and flexible building blocks for multipurpose utilizations.Over the past decade,a variety of multifunctional reagents have been developed.However,most versatile reagents usually need multi-step synthesis,thus restricting their wide application to a large extent.In terms of the practicalities and universalities,we prefer to pay more attention to the utilization of simple and practical versatile reagents with multiple reactivities,mainly including atropaldehyde acetals,aryl methyl ketones,vinylene carbonate,vinyl azides,aryldiazonium salts,rongalite,halodifluoromethyl compounds.Most importantly,these versatile reagents can also play different roles simultaneously in the same reaction,in which their different reactivities are converged into the final target products.Such strategy can not only offer more possibilities for the synthesis of several active pharmaceutical ingredients,but also minimize the occurrence of some side reactions by lessening the varieties of materials.Also,a perspective is given at the end of this review. 展开更多
关键词 Versatile reagents Divergent synthesis Dual synthons Bond cleavage Tandem reactions
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Waste-minimized C(sp^(3))-H activation for the preparation of fused N-heterocycles
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作者 Nihad Salameh Francesco Minio +2 位作者 Gabriele Rossini Assunta Marrocchi luigi vaccaro 《Green Synthesis and Catalysis》 2023年第3期240-245,共6页
By exploiting the combined use of a heterogeneous recyclable palladium(II)-bis(N-heterocyclic carbene)catalyst and cyclopentyl methyl ether(CPME)as a convenient recoverable safer reaction medium,an effective wastemini... By exploiting the combined use of a heterogeneous recyclable palladium(II)-bis(N-heterocyclic carbene)catalyst and cyclopentyl methyl ether(CPME)as a convenient recoverable safer reaction medium,an effective wasteminimized approach has been developed for the intramolecular Pd-catalyzed C(sp3)-H activation of methyl pyrrole derivatives.This synthetic tools has allowed to access condensed N-heterocycles generally endowed with biological activities and representatively are the core motif of complex molecules such as Mitomycines and Tylophorines.The heterogeneous catalytic system could be recovered and reused up to representative five runs without any loss in efficiency.The target products(19 examples)have been obtained selectively and with excellent isolated yields up to 93%.The approach leads to the definition of a protocol with a very good E-factor(21)which is much lower(up to 98%)than those of comparable literature examples.Other green metrics have been calculated and the data collected demonstrate that our newly developed protocol is very promising in terms of its environmental impact profile. 展开更多
关键词 C-H functionalization C-H activation Sustainable chemistry Waste-minimization Heterogeneous catalysis Safe reaction medium
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Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination
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作者 Giulia Brufani Federica Valentini +4 位作者 Gabriele Rossini Lucia Rosignoli Yanlong Gu Ping Liu luigi vaccaro 《Green Synthesis and Catalysis》 2023年第2期154-159,共6页
Metal contamination is a waste-generating and serious issue in the synthesis of chemicals,in particular in the case of products with biological activity.The appropriate selection of operating conditions plays a crucia... Metal contamination is a waste-generating and serious issue in the synthesis of chemicals,in particular in the case of products with biological activity.The appropriate selection of operating conditions plays a crucial role in the abatement of metal leaching in solution and associated wastes.Herein we report a waste-minimized continuous flow process for the synthesis of 1,4-disubstitutedβ-keto 1,2,3-triazoles exploiting the use of a copper tube flow reactor(CTFR).The selection of the proper azeotropic mixture allowed an almost quantitative recovery of the reaction medium greatly influencing the E-factor of the protocol.A thorough understanding of the main parameters affecting the waste generation was given by calculation of the E-factor distribution for different work-up tested under batch and flow conditions.Furthermore,the measurement of different green metrics(AE:Atom Economy,SF:Stoichiometric Factor,RME:Reaction Mass Efficiency,and MRP:Mass Recover Parameter)clearly demonstrated the benefits of the flow scale-up that allowed to perform a low environmental footprint CuAAC reaction. 展开更多
关键词 Flow chemistry CUAAC AZEOTROPE Waste-minimization Copper tube flow reactor
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