214360-66-4

Usage

Uses

4-t-Butylphenylboronic acid, pinacol ester

InChI:InChI=1/C16H25BO2/c1-14(2,3)12-8-10-13(11-9-12)17-18-15(4,5)16(6,7)19-17/h8-11H,1-7H3

Upstream product

• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7598-28-9 4-tert-butylphenyltosylate 
• 73183-34-3 bis(pinacol)diborane 
• 59970-38-6 4-tert-butylphenyl mesylate 
• 3972-56-3 4-(tert-butyl)chlorobenzene 
• 769-92-6 4-tert-Butylaniline 
• 1319748-01-0 1-[2-(4-tert-butylphenyl)diazen-1-yl]pyrrolidine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 241147-96-6 2-(4-(tert-butyl)phenyl)benzo[d][1,3,2]dioxaborole 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 

Downstream Products

• 927811-33-4 bis(4'-tert-butylbiphenylyl)methanone 
• 1174926-56-7 C₅₇H₄₄N₄S₂ 
• 688803-89-6 C₂₆H₂₈N₂S 
• 1152616-36-8 C₂₀H₁₈F₃N₃ 
• 849727-72-6 2-(2-bromo-4-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 701-30-4 1-tert-butyl-4-fluorobenzene 
• 231627-97-7 2-(4-(tert-butyl)phenyl)-4H-chromen-4-one 
• 1233691-86-5 1-(4-(tert-butyl)phenyl)naphthalene 
• 912341-51-6 1,1,2,2-tetrakis(4'-tert-butylbiphenyl-4-yl)ethene 

Relevant academic research and scientific papers

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

Remote steric control for undirected meta-selective C-H activation of arenes

Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.

Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation

The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C-O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

Para-selective borylation of monosubstituted benzenes using a transient mediator

Herein, we conceptualized a transient mediator approach that has the capability of para-selective C-H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.

Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?

Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.

Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides. This journal is