Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition–Redox Isomerization Catalyzed by Rhodium

2021 ◽  
Author(s):  
Brian J. Spinello ◽  
Jessica Wu ◽  
Yoon Cho ◽  
Michael J. Krische
Keyword(s):  
Primary Alcohols ◽  
Carbonyl Addition ◽  
Redox Isomerization

scholarly journals Formation of C–C bonds via ruthenium-catalyzed transfer hydrogenation

2012 ◽  
Vol 84 (8) ◽  
pp. 1729-1739 ◽  
Author(s):  
Joseph Moran ◽  
Michael J. Krische
Keyword(s):  
Transfer Hydrogenation ◽  
Primary Alcohols ◽  
Organometallic Reagents ◽  
Oxidation Level ◽  
Bond Forming ◽  
Carbonyl Addition ◽  
Aldehyde Oxidation

Ruthenium-catalyzed transfer hydrogenation of diverse π-unsaturated reactants in the presence of aldehydes provides products of carbonyl addition. Dehydrogenation of primary alcohols in the presence of the same π-unsaturated reactants provides identical products of carbonyl addition. In this way, carbonyl addition is achieved from the alcohol or aldehyde oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. In this account, the discovery of ruthenium-catalyzed C–C bond-forming transfer hydrogenations and the recent development of diastereo- and enantioselective variants are discussed.

Addition of primary alcohols to 3-chlorononafluoro-1,5-hexadiene and perfluoro-1,3,5-hexatriene

1985 ◽  
Vol 50 (8) ◽  
pp. 1714-1726 ◽  
Author(s):  
Václav Dědek ◽  
Igor Linhart ◽  
Milan Kováč
Keyword(s):  
Sulfuric Acid ◽  
Primary Alcohols ◽  
Principal Product ◽  
Allyl Rearrangement ◽  
Concentrated Sulfuric Acid ◽  
Sodium Alkoxide

Sodium alkoxide-catalyzed addition of methanol, ethanol and propanol to 3-chlorononafluoro-1,5-hexadiene (I) proceeds at temperatures -35 °C to 8 °C with allyl rearrangement, affording 1,6-dialkoxy-1,1,2,3,4,4,5,6,6-octafluoro-2,4-hexadiene (V) as the principal product, along with 1,6-dialkoxy-1,2,3,3,4,5,6,6-octafluoro-1,5-diene (VI) and trans-1,6-dialkoxy-1,1,2,3,4,4,5,6,6-nonafluoro-2-hexene (VII). The ethers Va-Vc consist of the cis,trans- and trans,trans-isomers in about 3 : 1 ratio, whereas the ethers VIa-VIc have trans,trans-configuration. Ethers Vc and VIc react with concentrated sulfuric acid to give dipropyl 2,3,4,5-tetrafluoro-2,4-hexadienedioate (IX) and dipropyl 2,3,4,4,5-pentafluoro-2-hexenedioate (X), respectively, whereas the ether VIIc affords a mixture of propyl 6-propyloxy-2,3,4,4,5,6-heptafluoro-2-hexenoate (XI) and ester X. Addition of methanol to perfluoro-1,3,5-hexatriene (II) affords 1,1,2,3,4,5,6,6-octafluoro-1,6-dimethoxy-3-hexene (XIII) as the principal product.

Cross β-alkylation of primary alcohols catalysed by DMF-stabilized iridium nanoparticles

2021 ◽  
Author(s):  
Masaki Kobayashi ◽  
Hiroki Yamaguchi ◽  
Takeyuki Suzuki ◽  
Yasushi Obora
Keyword(s):  
Primary Alcohols ◽  
Recycling Process ◽  
Catalyst Recycling ◽  
Simple Method ◽  
Benzyl Alcohols ◽  
Effective Catalyst ◽  
Iridium Nanoparticles ◽  
Highly Effective ◽  
Linear Alcohols ◽  
The Cross

A simple method for the cross β-alkylation of linear alcohols with benzyl alcohols in the presence of DMF-stabilized iridium nanoparticles was developed. Furthermore, a highly effective catalyst-recycling process was also developed.

BnA1.CER4 and BnC1.CER4 are redundantly involved in branched primary alcohols in the cuticle wax of Brassica napus

2021 ◽  
Author(s):  
Jie Liu ◽  
Lixia Zhu ◽  
Benqi Wang ◽  
Huadong Wang ◽  
Imran khan ◽  
...  
Keyword(s):  
Brassica Napus ◽  
Primary Alcohols

A novel, one-step method for the conversion of primary alcohols into carbamate-protected amines

2002 ◽  
Vol 43 (21) ◽  
pp. 3887-3890 ◽  
Author(s):  
Michael R. Wood ◽  
June Y. Kim ◽  
Kathy M. Books
Keyword(s):  
Primary Alcohols ◽  
Step Method ◽  
One Step
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