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

• 25240-59-9 pinacolboronic acid 
• 154318-75-9 4-tert-butylphenyl triflate 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 98-54-4 para-tert-butylphenol 
• 36600-66-5 4-tert-butylphenylhydrazine hydrochloride 
• 73183-34-3 bis(pinacol)diborane 
• 253185-03-4 tert-butylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 2909-79-7 4-tert-butyl-N,N-dimethylaniline 
• 15084-51-2 4-tert-butylbenzenesulfonyl chloride 
• 226569-78-4 1-tert-butyldimethylsilyloxy-4-tert-butylbenzene 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 28460-09-5 N,N-diethyl-4-tert-butylphenyl carbamate 

Downstream Products

• 927811-33-4 bis(4'-tert-butylbiphenylyl)methanone 
• 849727-72-6 2-(2-bromo-4-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1537171-80-4 1-(tert-butyl)-4-(1,1-difluoroallyl)benzene 
• 1537172-04-5 1-(tert-butyl)-4-(3,3-difluoroallyl)benzene 
• 728920-14-7 C₃₇H₄₁NO₂ 
• 728904-28-7 3,6-bis(-(4-tert-butyl)phenyl)-9H-carbazole 
• 1401699-57-7 9,9'-(6,6'-dimethoxybiphenyl-3,3'-diyl)bis(3,6-bis(4-tert-butylphenyl)-9H-carbazole) 
• 1152616-36-8 C₂₀H₁₈F₃N₃ 
• 688803-89-6 C₂₆H₂₈N₂S 
• 1174926-56-7 C₅₇H₄₄N₄S₂ 
• 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

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.

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

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.

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.

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.

Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate

The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.