73739-88-5Relevant academic research and scientific papers
Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated from tert -Alkyl N -Phthalimidoyl Oxalates by Visible-Light Photocatalysis
Lackner, Gregory L.,Quasdorf, Kyle W.,Pratsch, Gerald,Overman, Larry E.
, p. 6012 - 6024 (2015)
The coupling of tertiary carbon radicals with alkene acceptors is an underdeveloped strategy for uniting complex carbon fragments and forming new quaternary carbons. The scope and limitations of a new approach for generating nucleophilic tertiary radicals
Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light
Chowdhury, Rajdip,Yu, Zhunzhun,Tong, My Linh,Kohlhepp, Stefanie V.,Yin, Xiang,Mendoza, Abraham
, p. 20143 - 20151 (2020/11/13)
Photoexcited dihydronicotinamides like NADH and analogues have been found to generate alkyl radicals upon reductive decarboxylation of redox-active esters without auxiliary photocatalysts. This principle allowed aliphatic photocoupling between redox-activ
Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling
Nawrat, Christopher C.,Jamison, Christopher R.,Slutskyy, Yuriy,MacMillan, David W. C.,Overman, Larry E.
, p. 11270 - 11273 (2015/09/21)
Alkyl oxalates are new bench-stable alcohol-activating groups for radical generation under visible light photoredox conditions. Using these precursors, the first net redox-neutral coupling of tertiary and secondary alcohols with electron-deficient alkenes is achieved.
Constructing Quaternary Carbons from N -(Acyloxy)phthalimide Precursors of Tertiary Radicals Using Visible-Light Photocatalysis
Pratsch, Gerald,Lackner, Gregory L.,Overman, Larry E.
, p. 6025 - 6036 (2015/06/30)
Tertiary carbon radicals have notable utility for uniting complex carbon fragments with concomitant formation of new quaternary carbons. This article explores the scope, limitations, and certain mechanistic aspects of Okada's method for forming tertiary c
A practical and catalytic reductive olefin coupling
Lo, Julian C.,Yabe, Yuki,Baran, Phil S.
supporting information, p. 1304 - 1307 (2014/02/14)
A redox-economic method for the direct coupling of olefins that uses an inexpensive iron catalyst and a silane reducing agent is reported. Thus, unactivated olefins can be joined directly to electron-deficient olefins in both intra- and intermolecular settings to generate hindered bicyclic systems, vicinal quaternary centers, and even cyclopropanes in good yield. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. Most importantly, it allows access to many compounds that would be difficult or perhaps impossible to access using other methods.
Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates
Lackner, Gregory L.,Quasdorf, Kyle W.,Overman, Larry E.
supporting information, p. 15342 - 15345 (2013/11/06)
A convenient method for the direct construction of quaternary carbons from tertiary alcohols by visible-light photoredox coupling of tert-alkyl N-phthalimidoyl oxalate intermediates with electron-deficient alkenes is reported.
