Transition metal-free synthesis of alkyl pinacol boronates DOI
Kanak Kanti Das,

Swagata Paul,

Santanu Panda

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(44), P. 8939 - 8974

Published: Jan. 1, 2020

This review systematically outlined the research in area of transition metal free synthesis alkyl pinacol boronates, which are versatile and important scaffolds to construct diverse organic compounds.

Language: Английский

Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross‐Coupling DOI

Jesse A. Myhill,

Liang Zhang, Gabriel J. Lovinger

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(39), P. 12799 - 12803

Published: Aug. 9, 2018

Abstract Catalytic enantioselective conjunctive cross‐coupling has been developed to construct tertiary alkylboronic esters. These reactions occur with good yield and enantioselectivity for a range of substrates. Mechanistic experiments reveal aspects the catalytic cycle that allow hindered substrates react without significant complicating side reactions.

Language: Английский

Citations

58
Radical-Polar Crossover Reactions of Dienylboronate Complexes: Synthesis of Functionalized Allylboronic Esters DOI Creative Commons
Marvin Kischkewitz,

Carolin Gerleve,

Armido Studer

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(12), P. 3666 - 3669

Published: June 6, 2018

Radical-polar crossover reactions of dienylboronate complexes are applied to the synthesis functionalized secondary and tertiary allylboronic esters. The transition-metal-free three-component coupling uses readily accessible esters as substrates in combination with various sp3/sp2 carbon nucleophiles commercial alkyl iodides radical precursors. In visible light-initiated chain process, two new C–C bonds formed, E-double bond geometry product is controlled good excellent selectivity.

Language: Английский

Citations

53
Catalytic protodeboronation of pinacol boronic esters: formal anti-Markovnikov hydromethylation of alkenes DOI Creative Commons

Florian Clausen,

Marvin Kischkewitz,

Klaus Bergander

et al.

Chemical Science, Journal Year: 2019, Volume and Issue: 10(24), P. 6210 - 6214

Published: Jan. 1, 2019

Methane is formally added to alkenes via sequential hydroboration, Matteson-CH2-homologation and radical protodeboronation.

Language: Английский

Citations

53
Alternating Radical Stabilities: A Convergent Route to Terminal and Internal Boronates DOI
Qi Huang,

Jean Michalland,

Samir Z. Zard

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(47), P. 16936 - 16942

Published: June 27, 2019

Pinacolato boronates (Bpin) with an empty p-orbital on boron stabilize adjacent carbon radical, in contrast to diethanolamino [B(DEA)] where the is sp3 -hybridized. By alternately placing a pinacol or diethanolamine moiety atom, thus stabilizing not corresponding it possible control behavior of α-boronyl xanthates and construct large variety terminal internal modular fashion. The remarkable tolerance polar groups ability introduce quaternary centers are particularly noteworthy features this process.

Language: Английский

Citations

45
Transition metal-free synthesis of alkyl pinacol boronates DOI
Kanak Kanti Das,

Swagata Paul,

Santanu Panda

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(44), P. 8939 - 8974

Published: Jan. 1, 2020

This review systematically outlined the research in area of transition metal free synthesis alkyl pinacol boronates, which are versatile and important scaffolds to construct diverse organic compounds.

Language: Английский

Citations

45