Journal ArticleDOI
C−H Activation for the Construction of C−B Bonds
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Investigations revealed that the conversion of C-H bonds to C-B bonds was both thermodynamically and kinetically favorable and highlighted the accessible barriers for C- H bond cleavage and B-C bond formation during the borylation of alkanes and arenes.Abstract:
A number of studies were conducted to demonstrate C-H activation for the construction of C-B bonds. Investigations revealed that the conversion of C-H bonds to C-B bonds was both thermodynamically and kinetically favorable. The reaction at a primary C-H bond of methane or a higher alkene B 2(OR)4 formed an alkylboronate ester R' -B(OR)2 and the accompanying borane H-B(OR2. The ester and the borane were formed on the basis of calculated bond energies for methylboronates and dioaborolanes. The rates of key steps along the reaction pathway for the conversion of a C-H bond in an alkane or arene to the C-B bond in an alkyl or arylboronate ester were favorable. These studies also highlighted the accessible barriers for C-H bond cleavage and B-C bond formation during the borylation of alkanes and arenes.read more
Citations
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Carboxylate-assisted transition-metal-catalyzed C-H bond functionalizations: mechanism and scope.
TL;DR: This review summarizes the development and scope of carboxylates as cocatalysts in transition-metal-catalyzed C-H functionalizations until autumn 2010 and proposes new acronyms, such as CMD (concerted metalationdeprotonation), IES (internal electrophilic substitution), or AMLA (ambiphilic metal ligand activation), which describe related mechanisms.
Journal ArticleDOI
C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals
TL;DR: This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.
Journal ArticleDOI
Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
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Recent advances in the transition metal-catalyzed twofold oxidative C–H bond activation strategy for C–C and C–N bond formation
TL;DR: This critical review covers the recent progresses on the regioselective dehydrogenative direct coupling reaction of heteroarenes, including arylation, olefination, alkynylation, and amination/amidation mainly utilizing transition metal catalysts.
Journal ArticleDOI
Direct C-H transformation via iron catalysis.
References
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Journal ArticleDOI
Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions
Tamio Hayashi,Kaori Yamasaki +1 more
Journal ArticleDOI
Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins
Shinji Murai,Fumitoshi Kakiuchi,S. Sekine,Yasuo Tanaka,Asayuki Kamatani,Motohiro Sonoda,Naoto Chatani +6 more
TL;DR: The selective cleavage of carbon-hydrogen bonds in organic compounds is a critical step in many organic syntheses, and is particularly important in the conversion of hydrocarbons to useful organic compounds.
BookDOI
Boronic acids : preparation and applications in organic synthesis and medicine
TL;DR: In this article, the authors present a list of Boronic acid derivatives and their application in the following: 1.1 Introduction. 2.2 Borylation of Aromatic Halides and Trif lates.
Journal ArticleDOI
Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.
TL;DR: It is reported that Ir(I) precursors in conjunction with bipyridine ligands catalyze in high yields the borylation of arenes under mild conditions, and that the reactions involve uncommon, Ir(II) tris-boryl complexes.
Journal ArticleDOI
Remarkably Selective Iridium Catalysts for the Elaboration of Aromatic C-H Bonds
TL;DR: A family of Ir catalysts now enables the direct synthesis of arylboron compounds from aromatic hydrocarbons and boranes under “solventless” conditions because they are highly selective for C–H activation and do not interfere with subsequent in situ transformations, including Pd-mediated cross-couplings with aryL halides.