Ni-Catalyzed Synthesis of Multisubstituted Allenes via Reductive Cross-Coupling of Propargylic Acetates with Chlorohydrosilanes

被引:1
作者
Yan, Xiaohui [1 ]
Deng, Hong [1 ]
机构
[1] Huaibei Normal Univ, Sch Chem & Mat Sci, Key Lab Green & Precise Synthet Chem & Applicat, Minist Educ,Anhui Prov Key Lab Synthet Chem & Appl, Huaibei 235000, Anhui, Peoples R China
关键词
Ni-catalyzed; Reductive cross-coupling; Multisubstituted allenes; Propargylic acetates; Chlorohydrosilanes; ASYMMETRIC-SYNTHESIS; TETRASUBSTITUTED ALLENES; CYCLIZATION REACTIONS; HYDROSILYLATION; SUBSTITUTION; CARBONATES; ACCESS;
D O I
10.1002/ejoc.202401234
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper introduces an innovative strategy for the synthesis of multisubstituted allenes via nickel-catalyzed reductive cross-coupling reactions. The approach utilizes propargyl acetates and chlorosilanes to produce a variety of silyl-substituted allenes. The reaction conditions are notably mild, and the process is characterized by high chemo- and regioselectivity, as well as an impressive substrate scope. Furthermore, the method can be readily extended to the use of chlorogermane and chlorostannane, facilitating the synthesis of germanium or stannium-substituted allenes. This research not only offers a valuable strategy for the preparation of multisubstituted allenes but also significantly broadens the synthetic repertoire for the construction of highly functionalized molecules.
引用
收藏
页数:6
相关论文
共 75 条
[1]   Cyclization reactions of bis(allenes) for the synthesis of polycarbo(hetero) cycles [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (09) :3106-3135
[2]   Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes [J].
Brasholz, Malte ;
Reissig, Hans-Ulrich ;
Zimmer, Reinhold .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (01) :45-56
[3]  
Brook M.A., 2000, SILICON ORGANIC ORGA, V123
[4]   Synthesizing allenes today (1982-2006) [J].
Brummond, Kay M. ;
DeForrest, Jolie E. .
SYNTHESIS-STUTTGART, 2007, (06) :795-818
[5]   Group 14 Elements Hetero-Difunctionalizations via Nickel-Catalyzed Electroreductive Cross-Coupling [J].
Chen, Haifeng ;
Zhu, Chen ;
Yue, Huifeng ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (33)
[6]   Rare-Earth-Catalyzed Selective 1,4-Hydrosilylation of Branched 1,3-Enynes Giving Tetrasubstituted Silylallenes [J].
Chen, Wufeng ;
Jiang, Chunhui ;
Zhang, Jianying ;
Xu, Jiaqi ;
Xu, Lin ;
Xu, Xiufang ;
Li, Jianfeng ;
Cui, Chunming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (33) :12913-12918
[7]   Recent advances in catalytic asymmetric synthesis of allenes [J].
Chu, Wen-Dao ;
Zhang, Yan ;
Wang, Jianbo .
CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (20) :4570-4579
[8]   Cross-Electrophile C(sp2)-Si Coupling of Vinyl Chlorosilanes [J].
Duan, Jicheng ;
Wang, Ke ;
Xu, Guang-Li ;
Kang, Shaolin ;
Qi, Liangliang ;
Liu, Xue-Yuan ;
Shu, Xing-Zhong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (51) :23083-23088
[9]   Total Synthesis of Natural Lembehyne C and Investigation of Its Cytotoxic Properties [J].
Dzhemileva, Lilya U. ;
D'yakonov, Vladimir A. ;
Makarov, Alexey A. ;
Makarova, Elina Kh ;
Andreev, Evgeny N. ;
Dzhemilev, Usein M. .
JOURNAL OF NATURAL PRODUCTS, 2020, 83 (08) :2399-2409
[10]   ANTI STEREOSELECTIVITY IN THE PALLADIUM(0)-CATALYZED CONVERSION OF PROPARGYLIC ESTERS INTO ALLENES BY PHENYLZINC CHLORIDE [J].
ELSEVIER, CJ ;
STEHOUWER, PM ;
WESTMIJZE, H ;
VERMEER, P .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :1103-1105