Suzuki reaction of bromoallenes with arylboronic acids was successfully performed by using an air-stable hemilabile P-O coordinated cyclopalladated complex Pd(Ph_2PCH_2CO_2)_2 as a precatalyst,and the corresponding co...Suzuki reaction of bromoallenes with arylboronic acids was successfully performed by using an air-stable hemilabile P-O coordinated cyclopalladated complex Pd(Ph_2PCH_2CO_2)_2 as a precatalyst,and the corresponding coupling products were obtained in satisfactory to excellent yields.All products are unknown compounds which were characterized by ~1H NMR,^(13)C NMR,IR,and HRMS.展开更多
Simultaneously forming a carbon-carbon and a carbon-heteroatom bond in a single step through transition metal-catalyzed alkene difunctionalization strategy has emerged as a powerful tool for synthetic organic chemistr...Simultaneously forming a carbon-carbon and a carbon-heteroatom bond in a single step through transition metal-catalyzed alkene difunctionalization strategy has emerged as a powerful tool for synthetic organic chemistry.Due to the uncontrollable reactivity,direct cross-coupling with bromoallenes as the building blocks for the selective allenation and borylation remains challenging.We herein report a new type of S-and P-stabilized bromoallenes for palladium-catalyzed modular allenation and borylation of alkenes to the divergent synthesis of multiply functionalized allenes in a highly regio-and diastereoselective manifold.The reaction features broad substrate scope and wide functional group compatibility,thus providing a straightforward method to install allenyl and boryl groups across alkenes.Control experiments highlight the crucial importance of S-,P-stabilization for the oxidative insertion of Pd-species into the allenyl-Br bond.The facile syntheses of bioactive allenic steroids and exocyclic allenes demonstrate the synthetic utility of this protocol.展开更多
A novel and convenient way has been developed for the preparation of bromoallenes from propargyl alcohols by the reagent combination of N-bromosuccinimide and dimethyl sulfide. Bromoallenes with high regioselectivity ...A novel and convenient way has been developed for the preparation of bromoallenes from propargyl alcohols by the reagent combination of N-bromosuccinimide and dimethyl sulfide. Bromoallenes with high regioselectivity were obtained in a convenient method.展开更多
Intermolecular addition-cyclization of 1, 3-dicarbonyl compounds with arylbromo- allenes in K2CO3 mediated condition afforded 2, 3, 4-trisubstituted furans in good yield.
The discovery of the novel reactivity of conjugated enynes,mediated by readily available halogenation reagents,opens a broad range of mechanistically unique pathways for the synthesis of highly functionalized chiral a...The discovery of the novel reactivity of conjugated enynes,mediated by readily available halogenation reagents,opens a broad range of mechanistically unique pathways for the synthesis of highly functionalized chiral allene derivatives.Bromoallenyl pyrrolidines can be synthesized via 1,4-addition of sulfonamide nitrogen nucleophiles and halogens to conjugated enynes.This process can lead to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under economical and environmentally friendly reaction conditions.展开更多
基金the National Natural Science Foundation of China(No.20603005) for financial supportpartly supported by the program for Changjiang Scholars and Innovative Research Teams in Universities (No.IRT0711)
文摘Suzuki reaction of bromoallenes with arylboronic acids was successfully performed by using an air-stable hemilabile P-O coordinated cyclopalladated complex Pd(Ph_2PCH_2CO_2)_2 as a precatalyst,and the corresponding coupling products were obtained in satisfactory to excellent yields.All products are unknown compounds which were characterized by ~1H NMR,^(13)C NMR,IR,and HRMS.
基金supported by the National Natural Science Foundation of China(22322108)Jiangsu Specially Appointed Professors Plan(SR10900122)the Natural Science Foundation of Jiangsu Province(BK20221355)。
文摘Simultaneously forming a carbon-carbon and a carbon-heteroatom bond in a single step through transition metal-catalyzed alkene difunctionalization strategy has emerged as a powerful tool for synthetic organic chemistry.Due to the uncontrollable reactivity,direct cross-coupling with bromoallenes as the building blocks for the selective allenation and borylation remains challenging.We herein report a new type of S-and P-stabilized bromoallenes for palladium-catalyzed modular allenation and borylation of alkenes to the divergent synthesis of multiply functionalized allenes in a highly regio-and diastereoselective manifold.The reaction features broad substrate scope and wide functional group compatibility,thus providing a straightforward method to install allenyl and boryl groups across alkenes.Control experiments highlight the crucial importance of S-,P-stabilization for the oxidative insertion of Pd-species into the allenyl-Br bond.The facile syntheses of bioactive allenic steroids and exocyclic allenes demonstrate the synthetic utility of this protocol.
基金the Fundamental Research Funds for the Central Universities(No.DUT12LK07).Dr.Bao thanks financial support from the Fundamental Research Funds for the Central Universities(No. DUT11SM01)
文摘A novel and convenient way has been developed for the preparation of bromoallenes from propargyl alcohols by the reagent combination of N-bromosuccinimide and dimethyl sulfide. Bromoallenes with high regioselectivity were obtained in a convenient method.
基金We are grateful to the National Natural Science Foundation of China(No.20472072,20332060).
文摘Intermolecular addition-cyclization of 1, 3-dicarbonyl compounds with arylbromo- allenes in K2CO3 mediated condition afforded 2, 3, 4-trisubstituted furans in good yield.
基金the University of Wisconsin-Madison and the American Chemical Society Petroleum Research Fund (48092-G) for funding
文摘The discovery of the novel reactivity of conjugated enynes,mediated by readily available halogenation reagents,opens a broad range of mechanistically unique pathways for the synthesis of highly functionalized chiral allene derivatives.Bromoallenyl pyrrolidines can be synthesized via 1,4-addition of sulfonamide nitrogen nucleophiles and halogens to conjugated enynes.This process can lead to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under economical and environmentally friendly reaction conditions.
