83947-56-2 Usage
Description
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is a chemical compound with a unique structure that features a styrene moiety attached to a tetramethyl-1,3,2-dioxaborolan-2-yl group. TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is known for its versatile reactivity and stability, making it a valuable building block in organic synthesis.
Uses
Used in Oxidative Coupling Reactions:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used as a reactant for oxidative coupling reactions catalyzed by arene ruthenium complexes. Its reactivity allows for the formation of new carbon-carbon bonds, which are essential in the synthesis of complex organic molecules.
Used in Cycloaddition Reactions:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is also employed in cycloaddition reactions, where it can participate in the formation of cyclic compounds. These reactions are crucial for the synthesis of various pharmaceuticals, agrochemicals, and materials.
Used in the Preparation of Allyl Vinyl Ethers:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used as a starting material for the preparation of allyl vinyl ethers via Cu-catalyzed coupling with alcohols. These allyl vinyl ethers are valuable intermediates in the synthesis of various organic compounds and polymers.
Used in the Preparation of 5-Vinyl-3-Pyridinecarbonitriles:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is utilized in the synthesis of 5-vinyl-3-pyridinecarbonitriles, which serve as potent protein kinase C theta (PKCθ) inhibitors. These inhibitors are important in the development of drugs targeting various diseases, including cancer and inflammatory conditions.
Used in Diastereoselective Addition to Zincated Hydrazones:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used in diastereoselective addition reactions to zincated hydrazones. This process allows for the selective formation of specific stereoisomers, which are crucial in the synthesis of enantioselective drugs and agrochemicals.
Used in Stereospecific Trapping of Boron/Zinc Bimetallic Intermediates:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is also employed in the stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles. This reaction is an important step in the synthesis of various chiral compounds and catalysts.
Used in Regioselective and Stereoselective Pd-Catalyzed Chelate-Controlled Intermolecular Oxidative Heck Reactions:
TRANS-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE is used in regioselective and stereoselective Pd-catalyzed chelate-controlled intermolecular oxidative Heck reactions. These reactions are essential for the formation of specific carbon-carbon bonds with high selectivity, which is crucial in the synthesis of complex organic molecules and pharmaceuticals.
Check Digit Verification of cas no
The CAS Registry Mumber 83947-56-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,9,4 and 7 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 83947-56:
(7*8)+(6*3)+(5*9)+(4*4)+(3*7)+(2*5)+(1*6)=172
172 % 10 = 2
So 83947-56-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H19BO2/c1-13(2)14(3,4)17-15(16-13)11-10-12-8-6-5-7-9-12/h5-11H,1-4H3/b11-10+
83947-56-2Relevant articles and documents
Synthesis of tri-substituted vinyl boronates via ruthenium-catalyzed olefin cross-metathesis
Morrill, Christie,Funk, Timothy W.,Grubbs, Robert H.
, p. 7733 - 7736 (2004)
Tri-substituted vinyl pinacol boronates are synthesized using cross-metathesis of α-substituted vinyl boronates. The reactions proceed with moderate yields and high Z-selectivity when R1 = methyl. When R1 is larger than a methyl group, yields and Z-selectivity are moderate at best, and the reactions are highly substrate dependent.
(Z)-Selective Hydroboration of Terminal Alkynes Catalyzed by a PSP-Pincer Rhodium Complex
Lyu, Yanzong,Toriumi, Naoyuki,Iwasawa, Nobuharu
supporting information, p. 9262 - 9266 (2021/11/30)
A highly (Z)-selective hydroboration of terminal alkynes was achieved using a thioxanthene-based PSP-pincer rhodium catalyst. This hydroboration exhibited good chemoselectivity toward alkynes over carbonyl compounds such as ketones and aldehydes. The mechanistic studies indicated the involvement of rhodium-vinylidene intermediates, and the high (Z)-selectivity could be attributed to the rigid and electron-rich nature of the PSP-rhodium catalyst.
Tropylium-Promoted Hydroboration Reactions: Mechanistic Insights Via Experimental and Computational Studies
Mai, Binh Khanh,Nguyen, Thanh Vinh,Ton, Nhan N. H.
supporting information, p. 9117 - 9133 (2021/07/19)
Hydroboration reaction of alkynes is one of the most synthetically powerful tools to access organoboron compounds, versatile precursors for cross-coupling chemistry. This type of reaction has traditionally been mediated by transition-metal or main group catalysts. Herein, we report a novel method using tropylium salts, typically known as organic oxidants and Lewis acids, to promote the hydroboration reaction of alkynes. A broad range of vinylboranes can be easily accessed via this metal-free protocol. Similar hydroboration reactions of alkenes and epoxides can also be efficiently catalyzed by the same tropylium catalysts. Experimental studies and DFT calculations suggested that the reaction follows an uncommon mechanistic pathway, which is triggered by the hydride abstraction of pinacolborane with tropylium ion. This is followed by a series ofin situcounterion-activated substituent exchanges to generate boron intermediates that promote the hydroboration reaction.
