Asymmetric Hydroarylation of Unsaturated Bond via C-H Functionalization by Cationic Iridium/Bisphosphoramidite Catalyst

2018 ◽  
Vol 76 (6) ◽  
pp. 604-614
Author(s):  
Tomohiko Shirai ◽  
Yasunori Yamamoto
Keyword(s):  
Unsaturated Bond

scholarly journals Recoverable Phospha-Michael Additions Catalyzed by a 4-N,N-Dimethylaminopyridinium Saccharinate Salt or a Fluorous Long-Chained Pyridine: Two Types of Reusable Base Catalysts

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1159
Author(s):  
Eskedar Tessema ◽  
Vijayanath Elakkat ◽  
Chiao-Fan Chiu ◽  
Jing-Hung Zheng ◽  
Ka Long Chan ◽  
...  
Keyword(s):  
Michael Addition ◽  
Polar Solvent ◽  
Addition Reaction ◽  
High Yield ◽  
Addition Reactions ◽  
Polar Solvents ◽  
Unsaturated Bond ◽  
Base Catalysts ◽  
Michael Additions

Phospha-Michael addition, which is the addition reaction of a phosphorus-based nucleophile to an acceptor-substituted unsaturated bond, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds, since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalized products. In this work, two kinds of basic pyridine-based organo-catalysts were used to efficiently catalyze phospha-Michael addition reactions, the 4-N,N-dimethylaminopyridinium saccharinate (DMAP·Hsac) salt and a fluorous long-chained pyridine (4-Rf-CH2OCH2-py, where Rf = C11F23). These catalysts have been synthesized and characterized by Lu’s group. The phospha-Michael addition of diisopropyl, dimethyl or triethyl phosphites to α, β-unsaturated malonates in the presence of those catalysts showed very good reactivity with high yield at 80–100 °C in 1–4.5 h with high catalytic recovery and reusability. With regard to significant catalytic recovery, sometimes more than eight cycles were observed for DMAP·Hsac adduct by using non-polar solvents (e.g., ether) to precipitate out the catalyst. In the case of the fluorous long-chained pyridine, the thermomorphic method was used to efficiently recover the catalyst for eight cycles in all the reactions. Thus, the easy separation of the catalysts from the products revealed the outstanding efficacy of our systems. To our knowledge, these are good examples of the application of recoverable organo-catalysts to the DMAP·Hsac adduct by using non-polar solvent and a fluorous long-chained pyridine under the thermomorphic mode in phospha-Michael addition reactions.

Factors Promoting Alkene Migratory Insertion into Metal-Nitrogen Bond during Hydroamination in Recent Studies

2021 ◽  
Vol 18 ◽  
Author(s):  
Wenlai Han
Keyword(s):  
Transition Metal ◽  
Late Transition Metal ◽  
Electronic Effects ◽  
Metal Centers ◽  
Unsaturated Bond ◽  
Factors Influencing ◽  
Migratory Insertion ◽  
Late Transition ◽  
Metal Catalyzed ◽  
Nitrogen Bond

: Migratory insertion is a fundamental organometallic transformation that enables the functionalization of an unsaturated bond. Recent reports on catalytic hydroamination provide evidence that supports an intermolecular migratory insertion pathway featuring alkene insertion into metal-nitrogen (M-N) bonds. This article presents factors influencing the rate of migratory insertion in late-transition metal-catalyzed hydroamination, including steric and electronic effects from ligands, alkenes, and metal centers, along with stabilization from coordinated amine intermediates and ordered transition states.

scholarly journals Gold-Catalyzed Cycloisomerization of o-Alkynylbenzaldehydes with a Pendant Unsaturated Bond: [3 + 2] Cycloaddition of Gold-Bound 1,3-Dipolar Species with Dipolarophiles.

ChemInform ◽  
2006 ◽  
Vol 37 (12) ◽  
Author(s):  
Nakjoong Kim ◽  
Yeongmi Kim ◽  
Wooram Park ◽  
Dokyung Sung ◽  
Aruna Kumar Gupta ◽  
...  
Keyword(s):  
Unsaturated Bond

Effect of the Unsaturated Bond on the Degradation of the Tetragalacturonic Acids by a Transeliminase

Nature ◽  
1964 ◽  
Vol 203 (4945) ◽  
pp. 649-649 ◽  
Author(s):  
MARTIN M. ANDERSON ◽  
CHARLES W. NAGEL
Keyword(s):  
Unsaturated Bond

Intramolecular Cyclization of Hydridophos-Phorane Containing Unsaturated Bond

1996 ◽  
Vol 26 (2) ◽  
pp. 287-290 ◽  
Author(s):  
Lun Zu Liu ◽  
Ao Zhang ◽  
Guo Wei Li ◽  
Lan Bing Fu
Keyword(s):  
Intramolecular Cyclization ◽  
Unsaturated Bond

scholarly journals The Catalytic Reduction of Unsaturated Bond with Cyanocobalt Complex Ion and its Side Reaction

1963 ◽  
Vol 84 (8) ◽  
pp. 669-673,A44 ◽  
Author(s):  
Masuo MURAKAMI ◽  
Ryutaro KAWAI ◽  
Kojiro SUZUKI
Keyword(s):  
Catalytic Reduction ◽  
Side Reaction ◽  
Unsaturated Bond ◽  
Complex Ion

On the Mechanism of Palladium‐Catalyzed Unsaturated Bond Transformations: A Review of Theoretical Studies

2019 ◽  
Vol 8 (8) ◽  
pp. 1194-1206 ◽  
Author(s):  
Qin Xiong ◽  
Haohua Chen ◽  
Tao Zhang ◽  
Chunhui Shan ◽  
Ruopeng Bai ◽  
...  
Keyword(s):  
Theoretical Studies ◽  
Unsaturated Bond ◽  
Palladium Catalyzed
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