Chromium-Catalyzed Selective Dimerization/Hydroboration of Allenes to Access Boryl-Functionalized Skipped (E,Z)-Dienes

被引:23
作者
Zhao, Yinsong [1 ]
Ge, Shaozhong [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
关键词
allenes; chromium; dimerization; homogeneous catalysis; hydroboration; STEREOSELECTIVE-SYNTHESIS; STRUCTURE ELUCIDATION; TRANSITION-METALS; ETHYLENE; CYCLOADDITIONS; DIMERIZATION; ALLYLATION; TRANSFORMATIONS; POLYMERIZATION; HYDROBORATION;
D O I
10.1002/anie.202012344
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A chromium-catalyzed dimerization/hydroboration of allenes is developed to access synthetically versatile boryl-functionalized skipped dienes with a catalyst generated in situ from CrCl2 and a pyridine-2,6-diimine ligand (PDI)-P-mes. A variety of allenes reacted with pinacolborane (HBpin) to afford the corresponding boryl-functionalized (E,Z)-1,4-dienes in high yields and with excellent selectivity. Electron paramagnetic resonance (EPR) spectroscopic studies suggest that this chromium-catalyzed reaction probably proceeds through a chromium(I) hydride intermediate.
引用
收藏
页码:2149 / 2154
页数:6
相关论文
共 77 条
[51]   Stereospecific functionalizations and transformations of secondary and tertiary boronic esters [J].
Sandford, Christopher ;
Aggarwal, Varinder K. .
CHEMICAL COMMUNICATIONS, 2017, 53 (40) :5481-5494
[52]   Selective[1,4]-Hydrovinylation of 1,3-Dienes with Unactivated Olefins Enabled by Iron Diimine Catalysts [J].
Schmidt, Valerie A. ;
Kennedy, C. Rose ;
Bezdek, Mate J. ;
Chirik, Paul J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (09) :3443-3453
[53]   Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis [J].
Schwarz, J. Luca ;
Schaefers, Felix ;
Tlahuext-Aca, Adrian ;
Lueckemeier, Lukas ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (40) :12705-12709
[54]   Highly Selective Copper-Catalyzed Hydroboration of Allenes and 1,3-Dienes [J].
Semba, Kazuhiko ;
Shinomiya, Masataka ;
Fujihara, Tetsuaki ;
Terao, Jun ;
Tsuji, Yasushi .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (22) :7125-7132
[55]   Asymmetric Hydrovinylation of Unactivated Linear 1,3-Dienes [J].
Sharma, Rakesh K. ;
RajanBabu, T. V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3295-+
[56]   In Situ EPR Monitoring of Chromium Species Formed during Cr-Pyrrolyl Ethylene Trimerization Catalyst Formation [J].
Skobelev, Igor Y. ;
Panchenko, Valentina N. ;
Lyakin, Oleg Y. ;
Bryliakov, Konstantin P. ;
Zakharov, Vladimir A. ;
Talsi, Evgenii P. .
ORGANOMETALLICS, 2010, 29 (13) :2943-2950
[57]   Exploration of Earth-Abundant Transition Metals (Fe, Co, and Ni) as Catalysts in Unreactive Chemical Bond Activations [J].
Su, Bo ;
Cao, Zhi-Chao ;
Shi, Zhang-Jie .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (03) :886-896
[58]  
Tao X., 2018, ANGEW CHEM INT EDIT, V130, P14118
[59]   Borane-Induced Dimerization of Arylallenes [J].
Tao, Xin ;
Daniliuc, Constantin G. ;
Dittrich, Dustin ;
Kehr, Gerald ;
Erker, Gerhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) :13922-13926
[60]   Stereospecific synthesis of highly substituted skipped dienes through multifunctional palladium catalysis [J].
Thadani, AN ;
Rawal, VH .
ORGANIC LETTERS, 2002, 4 (24) :4317-4320