23958-24-9Relevant academic research and scientific papers
Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP
Zhang, Yan,Xia, Mingze,Li, Min,Ping, Qian,Yuan, Zhenbo,Liu, Xuanzhong,Yin, Huimin,Huang, Shuping,Rao, Yijian
, p. 15284 - 15297 (2021/11/01)
Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.
Photoinitiated carbonyl-metathesis: Deoxygenative reductive olefination of aromatic aldehydes: Via photoredox catalysis
Wang, Shun,Lokesh, Nanjundappa,Hioe, Johnny,Gschwind, Ruth M.,K?nig, Burkhard
, p. 4580 - 4587 (2019/05/14)
Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the CC bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.
Olefin cross-metathesis/Suzuki-Miyaura reactions on vinylphenylboronic acid pinacol esters
Baltus, Christine B.,Chuckowree, Irina S.,Press, Neil J.,Day, Iain J.,Coles, Simon J.,Tizzard, Graham J.,Spencer, John
supporting information, p. 1211 - 1217 (2013/03/13)
A series of alkenyl phenylboronic acid pinacol esters has been synthesized via an olefin cross-metathesis reaction of vinylphenylboronic acid pinacol ester derivatives. After catalytic hydrogenation, the resulting boronates were coupled via a microwave-mediated Suzuki-Miyaura reaction to afford a library of biarylethyl aryl and biarylethyl cycloalkyl derivatives. A complementary reaction sequence involved an initial Suzuki-Miyaura coupling.
Convenient and stereoselective synthesis of symmetrical (E)-stilbenes via homocoupling of 1,3-dibenzylbenzotriazolium bromides
Xiao, Xiaohui,Lin, Daqin,Tong, Shuitian,Luo, Hong,He, Yinfeng,Mo, Hailan
supporting information; experimental part, p. 1731 - 1734 (2011/09/16)
Using NaH as the base and DMSO as the solvent, a series of symmetric (E)-stilbenes were prepared in good yields via the -homocoupling of 1,3-dibenzylbenzotriazolium bromides at room temperature. Georg Thieme Verlag Stuttgart · New York.
Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex
Chen, Yi-Jing,Chen, Chinpiao
, p. 1313 - 1319 (2008/02/09)
This study describes a C2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8′-(Hydroxy-diphenyl-methyl)-10,10,10′,10′-tetramethy l-[5,5′]bi[6-aza-tricyclo[7.1.1.02,7/s
Synthesis of trans-stilbenes utilising decarbonylation of α-chloro chloroformates mediated by samarium diiodide
Li, Zhifang,Zhang, Yongmin
, p. 340 - 341 (2007/10/03)
A new synthesis of trans-stilbenes has been achieved by decarbonylation of α-chloro chloroformates mediated by samarium diiodide in THF; this one pot reaction is completed within a few minutes at room temperature.
REACTIONS OF DIHALOCARBENES WITH SUBSTITUTED SPIROHEPTA-4,6-DIENES
Molchanov, A. P.,Kostikov, R. R.
, p. 935 - 937 (2007/10/02)
Reactions of dihalocarbenes with spirohepta-4,6-diene lead to the formation of 1-halo-3-(2-haloethyl)benzenes, which readily undergo dehydrohalogenation to 3-halostyrenes.From 1-arylspirohepta-4,6-dienes and dihalocarbenes 3-halostilbenes are obtained.
Thioaldehyde S-Oxide (Monosubstituted Sulfines) from Thioacylsilane S-Oxides. Synthesis and Fluorine- and Acid-Induced Z/E Isomerization. 2
Barbaro, G.,Battaglia, A.,Giorgianni, P.,Bonini, B. F.,Maccagnani, G.,Zani, P.
, p. 3744 - 3748 (2007/10/02)
Aromatic and aliphatic, not enethiolizable, thioaldehyde S-oxides (monosubstituted sulfines) are obtained from stereospecific fluorodesilylation of the corresponding thioacylsilane S-oxides with retention of configuration.A detailed investigation on the mechanism of the desilylation, as well as of the acid and fluoride ion induced Z/E interconversion has been performed.
ENCOUNTER OF AN INFERIOR INTRAMOLECULAR CYCLIZATION IN AN APPROACH TOWARD THE SYNTHESIS OF 10-OXO-2-THIAMETACYCLOPHANE:PREPARATION OF TWO ISOMERIC DIOXO-2,19-DITHIAMETACYCLOPHANES
Lai, Yee-Hing,Yeo, Lay-Hoon
, p. 1629 - 1636 (2007/10/02)
The sodium sulfide coupling of 1,2-bis(3-bromomethyl)phenylethanone, prepared in seven steps from m,α-dichlorotoluene, was attempted but failed to yield the desired 10-oxo-2-thia-metacyclophane.This is attributed to unfavorable geometry in the thiacy
ZEOLITE-CuNaY CATALYZED DECOMPOSITION OF ARYLDIAZOMETHANE
Onaka, Makoto,Kita, Hiroshi,Izumi, Yusuke
, p. 1895 - 1898 (2007/10/02)
Decomposition of aryldiazomethanes is catalyzed by copper ion-exchanged Y-type zeolite to afford cis-1,2-diarylethylenes in high selectivity.The catalytic activity and selectivity are found to be affected by the exchange level of copper ions in zeolite and the solvent used.
