86553-38-0

Upstream product

• 86553-35-7 Toluene-4-sulfonic acid 2-[((E)-3-phenyl-allyl)-(toluene-4-sulfonyl)-amino]-ethyl ester 
• 869275-29-6 N-allyl-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 108-86-1 bromobenzene 
• 129748-56-7 N-(2-bromoethyl)-N-(2-propenyl)-4-methylbenzenesulfonamide 
• 591-50-4 iodobenzene 
• 23665-09-0 phenylzinc iodide 
• 1078-58-6 diphenylzinc 
• 14316-14-4 N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 100-58-3 phenylmagnesium bromide 
• 5368-63-8 3-benzyl tetrahydrofurane 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 170304-83-3 3-benzylpyrrolidine 

Relevant academic research and scientific papers

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Vitamin B 12-Catalyzed Dicarbofunctionalization of Bromoalkenes under Visible Light Irradiation

Vitamin B 12plays a crucial role in enzymatic transformations. This natural compound proved also useful as a catalyst in numerous organic reactions. Commercial availability and lower cost than precious metal complexes, make cobalamin an attract

Mechanism of Ni-Catalyzed Reductive 1,2-Dicarbofunctionalization of Alkenes

Ni-catalyzed cross-electrophile coupling reactions have emerged as appealing methods to construct organic molecules without the use of stoichiometric organometallic reagents. The mechanisms are complex: plausible pathways, such as "radical chain" and "sequential reduction" mechanisms, are dependent on the sequence of the activation of electrophiles. A combination of kinetic, spectroscopic, and organometallic studies reveals that a Ni-catalyzed, reductive 1,2-dicarbofunctionalization of alkenes proceeds through a "sequential reduction" pathway. The reduction of Ni by Zn is the turnover-limiting step, consistent with Ni(II) intermediates as the catalyst resting-state. Zn is only sufficient to reduce (phen)Ni(II) to a Ni(I) species. As a result, commonly proposed Ni(0) intermediates are absent under these conditions. (Phen)Ni(I)-Br selectively activates aryl bromides via two-electron oxidation addition, whereas alkyl bromides are activated by (phen)Ni(I)-Ar through single-electron activation to afford radicals. These findings could provide insight into achieving selectivity between different electrophiles.

Ni-catalyzed two-component reductive dicarbofunctionalization of alkenes via radical cyclization

A reductive dicarbofunctionalization reaction of alkenes has been developed and applied to the preparation of substituted carbo- and heterocycles. The reaction conditions avoid the use of air-sensitive organometallic reagents, and are compatible with a broad range of bromo-electrophiles and a wide variety of substituents to give cyclic products in excellent yields.

Catalysis of Radical Cyclizations from Alkyl Iodides under H2: Evidence for Electron Transfer from [CpV(CO)3H]-

Radical cyclizations are most often achieved with Bu3SnH in the presence of a radical initiator, but environmental considerations demand that alternative reagents be developed - ones that can serve as a synthetic equivalent to the hydrogen atom. We have revisited [CpV(CO)3H]-, a known replacement for Bu3SnH, and found that it can be used catalytically under H2 in the presence of a base. We have carried out tin-free catalytic radical cyclizations of alkyl iodide substrates. The reactions are atom-efficient, and the conditions are mild, with broad tolerance for functional groups. We have, for example, achieved the first 5-exo radical cyclization involving attack onto a vinyl chloride. We suggest that the radicals are generated by an initial electron transfer.

Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products

We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, es

Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5 and Phenanthroline System

An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)5] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.

Iron-catalyzed tandem cyclization and cross-coupling reactions of iodoalkanes and aryl grignard reagents

A range of arylmethyl-substituted pyrrolidines and tetrahydrofurans were produced by FeCl2-catalyzed tandem cyclization and cross-coupling reactions of alkyl iodides and aryl Grignard reagents. The substituents on alkenes had a profound effect

Br?nsted acid-assisted N-alkylation of sulfonamides using ethers as the alkylation reagents

N-Alkylation of sulfonamides using cyclic ethers as alkylation reagents and Br?nsted acid as a catalyst produced pyrrolidine and piperidine derivatives in good yields. When using symmetrical and unsymmetrical ethers as alkylation reagents, mono-N-alkylation of sulfonamides took place to afford the corresponding products.

Water control over the chemoselectivity of a Ti/Ni multimetallic system: Heck- or reductive-type cyclization reactions of alkyl iodides

A versatile Ti/Ni multimetallic protocol is described for the efficient catalysis of two different reactions, namely a Heck- and reductive-type cyclization of alkyl iodides, in the absence or presence of water, respectively. Noteworthy, the versatility of