Synthesis of Tertiary Alkyl Amines from Terminal Alkenes: Copper-Catalyzed Amination of Alkyl Boranes

2012 ◽  
Vol 134 (15) ◽  
pp. 6571-6574 ◽  
Author(s):  
Richard P. Rucker ◽  
Aaron M. Whittaker ◽  
Hester Dang ◽  
Gojko Lalic
Keyword(s):  
Alkyl Amines ◽  
Terminal Alkenes ◽  
Tertiary Alkyl

ChemInform Abstract: Synthesis of Tertiary Alkyl Amines from Terminal Alkenes: Copper-Catalyzed Amination of Alkyl Boranes.

ChemInform ◽  
2012 ◽  
Vol 43 (38) ◽  
pp. no-no
Author(s):  
Richard P. Rucker ◽  
Aaron M. Whittaker ◽  
Hester Dang ◽  
Gojko Lalic
Keyword(s):  
Alkyl Amines ◽  
Terminal Alkenes ◽  
Tertiary Alkyl

The Thermal Decomposition of Alkoxycarbonyl Thiocyanates and Isothiocyanates

1975 ◽  
Vol 53 (6) ◽  
pp. 907-912 ◽  
Author(s):  
Dennis Liotta ◽  
Robert Engel
Keyword(s):  
Thermal Decomposition ◽  
Primary Alcohols ◽  
Reduced Pressure ◽  
Tertiary Alcohols ◽  
Alkyl Amines ◽  
Tertiary Alkyl

Alkoxycarbonyl thiocyanates and isothiocyanates have been decomposed thermally under reduced pressure at temperatures of 240–375°. Primary systems yield primarily alkyl thiocyanates, whereas secondary and tertiary systems yield alkyl isothiocyanates. The viability of using this reaction in a conversion of primary alcohols to primary alkyl thiols and secondary and tertiary alcohols to tertiary alkyl amines is discussed.

Tertiary Alkyl Amines: An Autoxidation-Dealkylation Process. II

1990 ◽  
Vol 10 (1-2) ◽  
pp. 69-74 ◽  
Author(s):  
Loris Grossi
Keyword(s):  
Alkyl Amines ◽  
Tertiary Alkyl

scholarly journals Ligand-Free Iron-Catalyzed Regiodivergent Hydroboration of Unactivated Terminal Alkenes

2020 ◽  
Author(s):  
Wei Su ◽  
Ruixiao Qiao ◽  
Xiaoli Zheng ◽  
Xia Tian ◽  
Jianrong Han ◽  
...  
Keyword(s):  
Considerable Progress ◽  
Open Chain ◽  
Free Iron ◽  
Factors Influencing ◽  
Ligand Free ◽  
Terminal Alkenes ◽  
Tertiary Alkyl

The control of regioselectivities has been recognized as the elementary issue for alkene hydroboration. Despite considerable progress, the specificity of alkene substrates or the adjustment of ligands were necessary for specific regioselectivities, which restrict the universality and practicability. Herein, we report a ligand-free iron-catalyzed regiodivergent hydroboration of unactivated terminal alkenes that obtains both Markovnikov and anti-Markovnikov hydroboration products in excellent regioselectivities. Notably, solvents and bases were shown to be crucial factors influencing the regioselectivities and further studies suggested the iron-boron alkoxide ate complex is the key intermediate that determines the unusual Markovnikov regioselectivity. Terminal alkenes with diverse structures (mono-substituted and 1,1-disubstituted, open-chain and exocyclic) underwent the transformation smoothly. The reaction does not require the addition of auxiliary ligands and it can be performed on a gram scale, thus providing an efficient and sustainable method for the synthesis of primary, secondary, and tertiary alkyl borates.

Facile C–N cleavage reactions of secondary and tertiary alkyl amines by P,O chelating rhodium and iridium complexes

2003 ◽  
Vol 6 (2) ◽  
pp. 202-205 ◽  
Author(s):  
Yasuhiro Yamamoto ◽  
Jouji Seta ◽  
Hiroshi Murooka ◽  
Xiao-Hong Han
Keyword(s):  
Iridium Complexes ◽  
Alkyl Amines ◽  
Cleavage Reactions ◽  
Tertiary Alkyl

scholarly journals Ligand-Free Iron-Catalyzed Regiodivergent Hydroboration of Unactivated Terminal Alkenes

2020 ◽  
Author(s):  
Wei Su ◽  
Ruixiao Qiao ◽  
Xiaoli Zheng ◽  
Xia Tian ◽  
Jianrong Han ◽  
...  
Keyword(s):  
Considerable Progress ◽  
Open Chain ◽  
Free Iron ◽  
Factors Influencing ◽  
Ligand Free ◽  
Terminal Alkenes ◽  
Tertiary Alkyl

The control of regioselectivities has been recognized as the elementary issue for alkene hydroboration. Despite considerable progress, the specificity of alkene substrates or the adjustment of ligands were necessary for specific regioselectivities, which restrict the universality and practicability. Herein, we report a ligand-free iron-catalyzed regiodivergent hydroboration of unactivated terminal alkenes that obtains both Markovnikov and anti-Markovnikov hydroboration products in excellent regioselectivities. Notably, solvents and bases were shown to be crucial factors influencing the regioselectivities and further studies suggested the iron-boron alkoxide ate complex is the key intermediate that determines the unusual Markovnikov regioselectivity. Terminal alkenes with diverse structures (mono-substituted and 1,1-disubstituted, open-chain and exocyclic) underwent the transformation smoothly. The reaction does not require the addition of auxiliary ligands and it can be performed on a gram scale, thus providing an efficient and sustainable method for the synthesis of primary, secondary, and tertiary alkyl borates.

An efficient high-yield synthesis for perfluorinated tertiary alkyl amines

2003 ◽  
Vol 123 (2) ◽  
pp. 233-236 ◽  
Author(s):  
Kyle W Felling ◽  
Richard J Lagow
Keyword(s):  
High Yield ◽  
Alkyl Amines ◽  
Tertiary Alkyl

ANIPE-Cu Catalyst Enables Highly Enantioselective Markovnikov Hydroboration of α-Olefins

Synlett ◽  
2020 ◽  
Author(s):  
Shi-Liang Shi ◽  
Yuan Cai
Keyword(s):  
Petrochemical Industry ◽  
Future Directions ◽  
Asymmetric Hydroboration ◽  
Terminal Alkenes ◽  
Cu Catalyst

AbstractAsymmetric hydroboration of simple and unactivated terminal alkenes (α-olefins), feedstock chemicals derived from the petrochemical industry, has not been efficiently realized for past decades. Using a bulky ANIPE ligand, we achieved a rare example of highly enantioselective copper-catalyzed Markovnikov hydroboration of α-olefins. The chiral secondary alkylboronic ester products were obtained in moderate to good yields and regioselectivities with excellent enantioselectivities.1 Introduction2 Conditions Optimization3 Substrate Scope4 Application5 Mechanistic Discussion6 Conclusions and Future Directions

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