Chan–Lam-Type C–S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

Lam, Long Yin; Ma, Cong

doi:10.1021/acs.orglett.1c02299

Cited by 23 publications

(16 citation statements)

References 36 publications

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“…We were particularly interested in sodium aryl sulfinates as the sulfur source for the safety, stability, ease of manipulation, and affordability. Previously, we reported the synthesis of thioethers catalyzed by cheap copper catalysts using commodity chemicals through C–S coupling between sodium aryl sulfinates and aryl halides, or organoboron compounds . Herein, we disclosed a new synthetic method for preparation of sulfonamides via a copper-catalyzed coupling reaction using functionalized sodium aryl sulfinates and amines.…”

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confidence: 99%

“…The increasing discovery of sulfur-containing medicines and bioactive compounds demonstrated the structural importance and attracted the attention of the pharmaceutical industry. , This protocol displayed a high tolerance of diverse functional groups substituted on both aryl amine and sodium arylsulfinate suitable for constructing the sulfonamide library in drug discovery and scale-up synthesis in a practical, economical, and green way. Together with our methods for thioether formation, , finding broad application in both academic and industrial environment is expected.…”

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confidence: 99%

“…Previously, we reported the synthesis of thioethers catalyzed by cheap copper catalysts using commodity chemicals through C−S coupling between sodium aryl sulfinates and aryl halides, 13 or organoboron compounds. 14 Herein, we disclosed a new synthetic method for preparation of sulfonamides via a copper-catalyzed coupling reaction using functionalized sodium aryl sulfinates and amines. By adopting this protocol, the sulfonamides can be synthesized using inexpensive and stable commodity chemicals in a green solvent system at a relatively low temperature.…”

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confidence: 99%

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Copper-Catalyzed Synthesis of Functionalized Aryl Sulfonamides from Sodium Sulfinates in Green Solvents

Lam

Chan

2022

J. Org. Chem.

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Functionalized aryl sulfonamides are important building blocks in the pharmaceutical industry. A one-step synthesis catalyzed by a copper salt was developed using stable solid commodity chemicals in sulfolane or, alternatively, in green solvents such as γ-valerolactone, iPrOAc, or nBuOAc with acetic acid. The method tolerated diverse functional groups commonly presented in current medicines and drug intermediates. The mechanistic study showed a radical coupling pathway between the sulfonyl and anilinium radicals through the use of K2S2O8 and copper catalyst, respectively.

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Copper-Catalyzed Synthesis of Functionalized Aryl Sulfonamides from Sodium Sulfinates in Green Solvents

Lam

Chan

2022

J. Org. Chem.

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“…When a Lagrangian has a Z 2 symmetry, m satisfies T m T T = m by a matrix T . Such Z 2 symmetries include µ-τ symmetry [2][3][4] and magic symmetry [31], which has been studied extensively. T is unitary because symmetry does not change the kinetic term, and T is also…”

Section: A Formula For the Minimal Type-i Seesaw Model And Conditions...mentioning

confidence: 99%

“…The symmetry generated by S 2 is called the magic symmetry and the matrix m is called magic in which the row sums and the column sums are all equal to a number α [31]. Since one of the eigenvectors is fixed to v 2 , an expression for m 2 is determined as…”

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Conditions of general $Z_{2}$ symmetry and TM$_{1,2}$ mixing for the minimal type-I seesaw mechanism in an arbitrary basis

Yang¹

2022

Preprint

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In this paper, using a formula for the minimal type-I seesaw mechanism by LDL T decomposition, conditions of general Z 2 -invariance of the neutrino mass matrix m is obtained for Lagrangian parameters in an arbitrary basis. The conditions are found to be (Mand the right-handed neutrino mass matrix M ij . In other words, the symmetric and antisymmetric part of b i must be proportional to those of the quantity (M 22 a i − M 12 b i ).Since the eigenvectors of the generator T are orthogonal, we can analyze the eigenvectors and mass eigenvalues of mm † for a Z 2 -symmetric m. Two eigenvectors u 1,2 of mm † coincide with any of those of T , and the remaining one is a vector (u 1 × u 2 ) * orthogonal to them. Furthermore, if the Yukawa matrix does not have the Z 2 symmetry, two nonzero neutrino masses are concisely represented.These results are applied to three Z 2 symmetries, the µ − τ symmetry, the TM 1 mixing, and the magic symmetry which predicts the TM 2 mixing. In particular, for the TM 2 mixing, the magic (anti-)symmetric Yukawa matrix with S 2 Y = ±Y is phenomenologically rejected because it predicts m 2 = 0 or m 1 , m 3 = 0. I. INTRODUCTIONThe structure of the lepton mixing matrix often involves a certain Z 2 symmetry of the neutrino mass matrix m. The bi-maximal mixing [1] accompanies the µ − τ symmetry [2-22], and the trimaximal mixing [23-30] does the magic symmetry [31]. The tri-bi-maximal (TBM) mixing [32] realized by the combination of these two mixings has the Klein symmetry K 4 ≃ Z 2 × Z 2 [33-35]. And for CP phases, µ − τ reflection symmetry [36-60] predicts the

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Multicomponent Selective Thioetherification of KSAc: Easy Access to Symmetrical/Unsymmetrical 4‐Alkylthio‐3‐halo‐2(5H)‐furanones

et al. 2023

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An easy two‐/three‐component selective thioetherification of KSAc for the synthesis of a series of symmetrical/unsymmetrical 4‐alkylthio‐3‐halo‐2(5H)‐furanones has been described. The reaction without any metal catalyst or additive is carried out in air atmosphere at room temperature for 5 h, only using potassium thioacetate as an odourless sulfur source and a base simultaneously. The broad substrate scope and high yield make it important for the studies on both constructing C−S bond based on non‐aryl Csp2−X bond and synthesizing new 2(5H)‐furanone functional molecules.

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Chan–Lam-Type C–S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds

Cited by 23 publications

References 36 publications

Copper-Catalyzed Synthesis of Functionalized Aryl Sulfonamides from Sodium Sulfinates in Green Solvents

Copper-Catalyzed Synthesis of Functionalized Aryl Sulfonamides from Sodium Sulfinates in Green Solvents

Conditions of general $Z_{2}$ symmetry and TM$_{1,2}$ mixing for the minimal type-I seesaw mechanism in an arbitrary basis

Multicomponent Selective Thioetherification of KSAc: Easy Access to Symmetrical/Unsymmetrical 4‐Alkylthio‐3‐halo‐2(5H)‐furanones

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