Photoinduced Deoxygenative Borylations of Aliphatic Alcohols DOI
Jingjing Wu, Robin M. Bär, Lin Guo

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(52), P. 18830 - 18834

Published: Oct. 15, 2019

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables novel Barton-McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without requirement photocatalyst, initiator, or tin silicon hydrides. The resultant alkyl intercepted by bis(catecholato)diboron, furnishing from diverse range structurally complex alcohols.

Language: Английский

Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis DOI Creative Commons
Danqing Zheng, Armido Studer

Organic Letters, Journal Year: 2018, Volume and Issue: 21(1), P. 325 - 329

Published: Dec. 21, 2018

A visible-light-initiated α-perfluoroalkyl-β-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis a range containing quinoxalin-2(1H)-one derivatives in moderate to excellent yields under mild conditions. Reactions proceed via acidic aminyl radicals that are readily deprotonated give the corresponding anions able sustain chain as single electron transfer reducing reagents. Hence, overall classifies electron-catalyzed process.

Language: Английский

Citations

154

New avenues for C–B bond formationviaradical intermediates DOI Creative Commons

Florian W. Friese,

Armido Studer

Chemical Science, Journal Year: 2019, Volume and Issue: 10(37), P. 8503 - 8518

Published: Jan. 1, 2019

Efficient radical routes to important alkyl and aryl boronic esters have been developed over the past few years. Such reactions are complementary existing transition-metal catalysed cross coupling processes.

Language: Английский

Citations

141

Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters DOI Creative Commons
Jinjiang Zhang, Xin‐Hua Duan, Yong Wu

et al.

Chemical Science, Journal Year: 2018, Volume and Issue: 10(1), P. 161 - 166

Published: Oct. 2, 2018

An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B2(OH)4 reagent not only served as boron source but also acted an electron donor through formation a complex with DMAc-like Lewis base.

Language: Английский

Citations

137

Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides DOI
Li Zhang, Lei Jiao

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(23), P. 9124 - 9128

Published: May 29, 2019

The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding diboron/methoxide/pyridine reaction system, we achieved photoactivation situ generated super electron donor and developed visible-light-induced organocatalytic method for efficient borylation chlorides.

Language: Английский

Citations

132

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols DOI
Jingjing Wu, Robin M. Bär, Lin Guo

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(52), P. 18830 - 18834

Published: Oct. 15, 2019

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables novel Barton-McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without requirement photocatalyst, initiator, or tin silicon hydrides. The resultant alkyl intercepted by bis(catecholato)diboron, furnishing from diverse range structurally complex alcohols.

Language: Английский

Citations

127