- Transition-Metal-Catalyzed Transformation of Sulfonates via S-O Bond Cleavage: Synthesis of Alkyl Aryl Ether and Diaryl Ether
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The catalytic conversion of sulfonates, a versatile class of pharmaceutical intermediates, is usually based on C-O bond cleavage. In this paper, however, we discover a rare transformation of sulfonates via S-O bond cleavage catalyzed by transition metal, through which alkyl sulfonates could undergo an intramolecular desulfitative C-O coupling to form aryl alkyl ethers in the presence of a nickel catalyst. Meanwhile, aryl sulfonates perform similarly to give diaryl ethers catalyzed by a palladium complex. This transformation could tolerate a wide range of functionalities. Controlled experiments reveal that the 2-pyridyl group is necessary to promote the reaction as designed. Crossover experiments proved that this transformation might proceed partly in an intermolecular pathway.
- Chen, Xuemeng,Xiao, Xue,Sun, Haotian,Li, Yue,Cao, Haolin,Zhang, Xuemei,Yang, Shengyong,Lian, Zhong
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supporting information
p. 8879 - 8883
(2019/11/14)
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- Palladium-catalyzed decarboxylative coupling of α-oxocarboxylic acids with C(sp2)-H of 2-aryloxypyridines
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An efficient palladium-catalyzed decarboxylative ortho-acylation of 2-aryloxypyridines with α-oxocarboxylic acids is described. In this new transformation, the aromatic C(sp2)-H bond was successfully acylated to give diverse aromatic ketones regioselectively in moderate to good yields. The pyridine group can be removed easily after the acylation to give the corresponding 2-hydroxy aromatic ketones. Copyright
- Yao, Jinzhong,Feng, Ruokun,Wu, Zaihong,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 1517 - 1522
(2013/06/27)
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- Heterobiaryl and heterobiaryl ether derived M5 positive allosteric modulators
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This Letter describes a chemical lead optimization campaign directed at VU0238429, the first M5-preferring positive allosteric modulator (PAM), discovered through analog work around VU0119498, a pan Gq mAChR M1, M3, M5 PAM. An iterative parallel synthesis approach was employed to incorporate basic heterocycles to improve physiochemical properties.
- Bridges, Thomas M.,Kennedy, J. Phillip,Hopkins, Corey R.,Conn, P. Jeffrey,Lindsley, Craig W.
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scheme or table
p. 5617 - 5622
(2010/11/05)
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- IMIDAZOPYRIDINE COMPOUND
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The present invention provides an imidazopyridine compound represented by formula (I), wherein R1 and R2 each independently represent a C1-6 alkyl group et al; R3 and R4 each independently represent a hydrogen atom, a methyl et al; Ar1 is a divalent substituent representing a monocyclic or bicyclic, 3- to 8-membered aromatic or aliphatic heterocyclic group et al; Ar2 represents an aromatic carbocyclic group, or an aromatic heterocyclic group; W represents -(CH2)m et al, and m indicates an integer of from 0 to 10. This compound acts as a melanin concentrating hormone receptor antagonist, and is useful as treating agents for obesity.
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Page/Page column 47
(2008/06/13)
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- A highly regioselective reaction of N-fluoropyridinium salts with stabilized sulfur, oxygen, and nitrogen nucleophiles: A convenient route to 2-substituted pyridines
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2-Substituted pyridines are efficiently obtained by the reactions of N- fluoropyridinium tetrafluoroborate or triflate with anions derived from benzenethiols, phenols, azoles, cyanamide, and with azide anion. The results are consistent with a nucleophile addition at the position 2 of the N- fluoropyridinium cation as the major reaction pathway.
- Kiselyov,Strekowski
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p. 1361 - 1364
(2007/10/02)
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