435344-57-3Relevant academic research and scientific papers
ROMPgel-supported biphenyl and naphthalene: Reagents for lithiation reactions with minimal purification
Arnauld, Thomas,Barrett, Anthony G.M.,Hopkins, Brian T.
, p. 1081 - 1083 (2002)
The synthesis of ring opening metathesis, polymer (ROMPgel) supported naphthalene and biphenyl reagents was carried out. These reagents were utilized for catalytic lithiation reactions of aryl and alkyl chlorides and for the reductive deprotection of benzyl and allyl ethers.
C(sp3)-H Bond Arylation and Amidation of Si-Bound Methyl Group via Directing Group Strategy
Han, Jie-Lian,Qin, Ying,Zhao, Dongbing
, p. 6020 - 6026 (2019/06/25)
Silylmethyl functionalization provides a general and efficient access to diverse organosilanes. The traditional methods for silylmethyl functionalization often involved silylmethylmetals or silylmethylhalides. In recent years, a C-H activation strategy has become one of the most attractive alternatives in organic synthesis. We envisioned that the attachment of a coordinating group at silicon of methylsilanes provides the opportunity to modify the silylmethyl group via directed C-H bond functionalization. However, despite employment of silicon tethers bearing a directing group (DG) for C(sp2)-H functionalization has been well established due to the fact that the silicon tethers are easily installable and removable/modifiable, applying this concept toward C(sp3)-H functionalization remains underdeveloped. Herein, we successfully develop IrIII/RhIII-catalyzed C-H bond arylation/amidation of silyl methyl group by using directing group strategy, which constitutes the most powerful access to benzylsilanes and amino-substituted silanes. Moreover, we demonstrated that the pyridine directing group on silicon atom can be easily removed, and the starting materials can also be efficiently recovered, which are different from those of pyridine-directed C-H functionalization of C-bound methyl group.
Tertiary α-Silyl Alcohols by Diastereoselective Coupling of 1,3-Dienes and Acylsilanes Initiated by Enantioselective Copper-Catalyzed Borylation
Feng, Jian-Jun,Oestreich, Martin
supporting information, p. 8211 - 8215 (2019/05/27)
An efficient synthesis of functionalized tertiary α-silyl alcohols by an enantio- and diastereoselective copper-catalyzed three-component coupling of 1,3-dienes, bis(pinacolato)diboron, and acylsilanes is reported. The reaction proceeds well with different 1,3-dienes and a broad range of aryl- as well as alkenyl- but also alkyl-substituted acylsilanes. The target compounds are formed with high regio-, diastereo-, and enantioselectivity (up to 99 % ee and d.r. >20:1) and are highly versatile synthetic building blocks.
Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents
Murakami, Kei,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 1415 - 1417 (2009/06/28)
Zinc-catalyzed nucleophilic substitution reactions of chlo-rosilanes with organomagnesium reagents afford various tetraorganosilanes under mild reaction conditions. The reactions can be performed on large scale and allow efficient preparation of functionalized tetraorganosilanes.
Synthesis of Optically Pure Arylsilylcarbinols and Their Use as Chiral Auxiliaries in Oxacarbenium Ion Reactions
Huckins, John R.,Rychnovsky, Scott D.
, p. 10135 - 10145 (2007/10/03)
A family of arylsilylcarbinols was synthesized and investigated as chiral auxiliaries for oxacarbenium ion reactions. The optically pure arylsilylcarbinols were prepared using Noyori's transfer hydrogenation catalyst 11. The transfer hydrogenation shows very good enantioselectivities and turnover efficiency for the aryl silyl ketones and is the method of choice for preparing these optically pure alcohols. The diastereoselective addition of allyltrimethylsilane to an in situ generated oxacarbenium ion was explored using Marko's conditions. The selectivity for a representative aliphatic aldehyde was very good, but the selectivity was significantly reduced with unsaturated and aromatic aldehydes. The range of selectivities with different auxiliaries was narrow, and the most practical auxiliary is the phenylsilylcarbinol 2.
