- Pd/P(i-BuNCH2CH2)3N: An efficient catalyst for Suzuki cross-coupling of aryl bromides and chlorides with arylboronic acids
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Pd(OAc)2 in combination with the commercially available ligand P(i-BuNCH2CH2)3N catalyzes the Suzuki cross-coupling reaction of a wide variety of aryl bromides and chlorides with arylboronic acids, affording the desired biaryls in excellent yields. It has also been shown that P(NMe2)3 can be employed as a ligand, though with significantly more limited success.
- Urgaonkar, Sameer,Nagarajan,Verkade
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- Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates
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We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox. We demonstrate the broad scope, scalability, and robustness of this unconventional catalyst-free transformation, leading to functionalized biaryls and ultimately furnishing drug-like small molecules, as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental investigations.
- Music, Arif,Baumann, Andreas N.,Spie?, Philipp,Plantefol, Allan,Jagau, Thomas C.,Didier, Dorian
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supporting information
p. 4341 - 4348
(2020/03/04)
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- Method of manufacturing hydroxybiphenyls
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PROBLEM TO BE SOLVED: To provide a convenient production method of biphenyls which become the raw materials of medicines, pesticides and functional materials. SOLUTION: In the presence of a palladium catalyst and an alkali metal carboxylate, a 2,2'-bi(1,3,2-benzodioxaborole) derivative represented by general formula (1) (in formula, R1represents a hydrogen atom or a 1-4C alkyl group) and a benzene derivative A are made to react with each other, next, in the presence of an alkali metal phosphate or an alkali metal carbonate, a benzene derivative B is made to react therewith, and biphenyls represented by general formula (4) (in formula, each of R2and R3represents a hydrogen atom, a halogen atom, or the like, and each of n and m represents an integer of 1 to 4) are produced. COPYRIGHT: (C)2013,JPOandINPIT
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Paragraph 0127-0128
(2020/11/19)
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- Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents. 32. NiCRAL's as Very Efficient Agents in Promoting Cross-Coupling of Aryl Halides
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Nickel-containing complex reducing agents NiCRA-bpy are shown to be the first nickel reagents able to efficiently perform cross-coupling of aryl halides.The presence of KI in the reaction medium generally improves the procedure.The mechanism and influence of the structures of the substrates are discused.
- Lourak, Mouhsine,Vanderesse, Regis,Fort, Yves,Caubere, Paul
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p. 4844 - 4848
(2007/10/02)
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- ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS 25. A ONE POT ONE REAGENT CROSS-COUPLING REACTION OF ARYL HALIDES
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The preparation of NiCRA in the presence of 2,2'-bipyridyl and KI leads to a reagent (termed NiCRA-bpy-KI) which is shown to be one of the most efficient Ni containing reagents reported so far for the cross-coupling of aryl halides.
- Lourak, M.,Vanderesse, R.,Fort, Y.,Caubere, P.
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p. 545 - 546
(2007/10/02)
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