Electroreductive Cross-Coupling between Aromatic Aldehydes and Chlorosilanes Enabling the Synthesis of α-Silyl Alcohols

被引:2
作者
Han, Fen [1 ]
Su, Qian [1 ]
Li, Yu [1 ]
Hao, Jianjun [1 ]
Peng, Yulin [1 ]
Zhang, Zhengbing [1 ]
Jing, Linhai [1 ]
Han, Pan [1 ]
机构
[1] China West Normal Univ, Coll Chem & Chem Engn, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Peoples R China
基金
中国国家自然科学基金;
关键词
BROOK REARRANGEMENT; NUCLEOPHILIC SILICON; CARBONYL-COMPOUNDS; ACYL SILANES; GENERATION; REDUCTION; ACYLSILANES; CHEMISTRY; CATALYST;
D O I
10.1021/acs.orglett.4c02607
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Silyl alcohols are powerful structural motifs for pharmaceutical chemistry, materials chemistry, and organic synthesis. The limitations of current synthetic techniques encompass a requirement for difficult-to-obtain silyl precursors, noble-metal catalysts, and narrow substrate scopes. Here, we developed a general synthetic method for alpha-silyl alcohols through electroreductive cross-coupling of aldehydes and chlorosilane. This method features easily available reagents, mild conditions, and a wide substrate scope. The establishment of this protocol will provide an alternative for access to alpha-silyl alcohols.
引用
收藏
页码:7037 / 7042
页数:6
相关论文
共 60 条
[1]   Asymmetric hydrogenation of aromatic, aliphatic, and α,β-unsaturated acyl silanes catalyzed by tol-binap/pica ruthenium(II) complexes:: Practical synthesis of optically active α-hydroxysilanes [J].
Arai, Noriyoshi ;
Suzuki, Ken ;
Sugizaki, Satoshi ;
Sorimachi, Hiroko ;
Ohkuma, Takeshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1770-1773
[2]   THE SYNTHESIS OF ALPHA-STANNYL-SILANES AND THEIR USE IN THE FORMATION OF ALKENES [J].
BARRETT, AGM ;
HILL, JM .
TETRAHEDRON LETTERS, 1991, 32 (28) :3285-3288
[3]   Silenes as novel synthetic reagents: identification of a practical method for silene generation and trapping [J].
Berry, MB ;
Griffiths, RJ ;
Sanganee, MJ ;
Steel, PG ;
Whelligan, DK .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (16) :2381-2392
[4]   Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions [J].
Box, John R. ;
Atkins, Alexander P. ;
Lennox, Alastair J. J. .
CHEMICAL SCIENCE, 2021, 12 (30) :10252-10258
[5]   Lewis base-promoted carbon-carbon sp3-sp3 coupling reactions of α-silyl silylethers [J].
Brekan, Jonathan A. ;
Chernyak, Dmitri ;
White, Kolby L. ;
Scheidt, Karl A. .
CHEMICAL SCIENCE, 2012, 3 (04) :1205-1210
[6]   ISOMERISM OF SOME ALPHA-HYDROXYSILANES TO SILYL ETHERS [J].
BROOK, AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (08) :1886-1889
[7]   SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].
BROOK, AG .
ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84
[8]   THE CONVERSION OF ACYL SILANES INTO CHIRAL SECONDARY ALCOHOLS [J].
BUYNAK, JD ;
STRICKLAND, JB ;
HURD, T ;
PHAN, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) :89-90
[9]   The synthesis of carbohydrate-derived acylsilanes and their intramolecular free radical cyclizations with the formation of polyoxygenated cyclopentanes [J].
Chang, Che-Chien ;
Kuo, Yu-Hsien ;
Tsai, Yeun-Min .
TETRAHEDRON LETTERS, 2009, 50 (27) :3805-3808
[10]   Silole-containing polymers: Chemistry and optoelectronic properties [J].
Chen, Junwu ;
Cao, Yong .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (17) :1714-1742