Unusual Regioselectivity in the Reductive Coupling of Alkynes and Allenes by Hydrozirconation and Zinca-Claisen Rearrangement

1997 ◽  
Vol 36 (22) ◽  
pp. 2469-2471 ◽  
Author(s):  
Keisuke Suzuki ◽  
Takahiro Imai ◽  
Shigeo Yamanoi ◽  
Masao Chino ◽  
Takashi Matsumoto
Keyword(s):  
Claisen Rearrangement ◽  
Reductive Coupling

Intramolecular Oxidative Coupling of Aromatic Compounds. VII. A Convenient Synthesis of (±)-Deoxyschizandrin

1994 ◽  
Vol 47 (8) ◽  
pp. 1579 ◽  
Author(s):  
AR Carroll ◽  
RW Read ◽  
WC Taylor
Keyword(s):  
Aromatic Compounds ◽  
Oxidative Coupling ◽  
Claisen Rearrangement ◽  
Oxidative Cleavage ◽  
Reductive Coupling ◽  
Convenient Synthesis

A convenient synthesis of (�)-deoxyschizandrin was achieved through the key step of reductive coupling of the bisacetonylbiphenyl (3). The latter compound was synthesized by oxidative cleavage of the bis olefin (5) formed by Claisen rearrangement of the bismethallyl ether of 2,2′,4,4′-tetramethoxybiphenyl-3,3′-diol. The synthesis of 2,2′,4,4′-tetramethoxy-6,6′-di(prop 1-enyl)biphenyl-3,3′-diol (2) is also described. The diphenolic oxidation of (2) did not lead to products with β,β′ carbons linked.

ChemInform Abstract: Unusual Regioselectivity in the Reductive Coupling of Alkynes and Allenes by Hydrozirconation and Zinca-Claisen Rearrangement.

ChemInform ◽  
2010 ◽  
Vol 29 (11) ◽  
pp. no-no
Author(s):  
K. SUZUKI ◽  
T. IMAI ◽  
S. YAMANOI ◽  
M. CHINO ◽  
T. MATSUMOTO
Keyword(s):  
Claisen Rearrangement ◽  
Reductive Coupling

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.

Metal-free Reductive Coupling of Biphenyl Tosylhydrazones with Phenols or Benzyl Alcohols

2017 ◽  
Vol 14 (10) ◽  
Author(s):  
Yang Liu ◽  
Ping Liu ◽  
Yan Liu ◽  
Yu Wei ◽  
Bin Dai
Keyword(s):  
Reductive Coupling ◽  
Benzyl Alcohols ◽  
Metal Free

Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

2014 ◽  
Vol 11 (9) ◽  
pp. 677-681 ◽  
Author(s):  
Van-Son Nguyen ◽  
Ling Shi ◽  
Yue Li ◽  
Qiu-An Wang
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Microwave Assistance

Photoreaction of N-butyl 3,4-dimethoxy-6-nitrobenzamide with butylamine. A model study for lysine-directed photoaffinity labelling

1987 ◽  
Vol 52 (7) ◽  
pp. 1780-1785 ◽  
Author(s):  
Petr Kuzmič ◽  
Libuše Pavlíčková ◽  
Milan Souček
Keyword(s):  
Nitro Group ◽  
Aromatic Ring ◽  
Ultraviolet Irradiation ◽  
Title Compound ◽  
Reductive Coupling ◽  
Photoaffinity Labelling ◽  
Photolysis Rate ◽  
Model Study ◽  
A Minor

Ultraviolet irradiation of the title compound I in the presence of butylamine gave predominantly products of nucleophilic photosubstitution by the amine, i.e., nitroanilines IIa and IIb. Besides, small amounts of products of hydrolysis (phenol III) and reductive coupling (azoxybenzene IV) were also formed. Comparison of the overall photolysis rate of I with that of 3,4-dimethoxy-1-nitrobenzene (V) indicates a minor loss of reactivity, most probably due to some deviation from coplanarity of the activating nitro group and the aromatic ring.

Direct reductive coupling of nitroarenes and alcohols catalysed by Co–N–C/CNT@AC

2019 ◽  
Vol 21 (8) ◽  
pp. 2129-2137 ◽  
Author(s):  
Di Liu ◽  
Ping Yang ◽  
Hao Zhang ◽  
Minjie Liu ◽  
Wenfei Zhang ◽  
...  
Keyword(s):  
Solvent Free ◽  
Reductive Coupling ◽  
Solvent Free Conditions

Imines and amines were synthesized on Co–N–C/CNT@AC by the coupling of nitroarenes and alcohols under base- and solvent-free conditions.

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