7697-58-7Relevant academic research and scientific papers
Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
supporting information, p. 2869 - 2872 (2017/06/13)
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
Stereo- and chemoselective cross-coupling between two electron-deficient acrylates: An efficient route to (Z, E)-muconate derivatives
Hu, Xu-Hong,Zhang, Jian,Yang, Xiao-Fei,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 3169 - 3172 (2015/03/30)
A Ru-catalyzed direct oxidative cross-coupling reaction of acrylates was developed. It offers a straightforward and atom-economical protocol for the synthesis of functionalized (Z,E)-muconate derivatives in moderate to good yields with good stereo- and chemoselectivities. The conjugated muconates bearing differentiable terminal functionality can be selectively transformed into versatile synthetic intermediates widely used in organic synthesis.
Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates
Feng, Chao,Feng, Daming,Loh, Teck-Peng
, p. 342 - 345 (2015/01/09)
Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.
Rhodium(III)-catalyzed olefinic C-H alkynylation of acrylamides using tosyl-imide as directing group
Feng, Chao,Feng, Daming,Luo, Yang,Loh, Teck-Peng
, p. 5956 - 5959 (2015/01/08)
The Rh(III)-catalyzed C-H alkynylation of acrylamide derivative is realized using a hypervalent alkynyl iodine reagent. The use of a weakly coordinating directing group proved to be of critical importance. This reaction displays broad functional group tolerance and high efficiency, which opens a new synthetic pathway to access functionalized 1,3-enyne skeletons.
Directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes
Feng, Chao,Loh, Teck-Peng
, p. 122414 - 122417 (2013/12/04)
Assistance provided: The directing group in the title reaction not only activates the substrates but also allows the stereospecific formation of cis-trifluoromethylated products. The reaction is operationally simple and tolerates a wide variety of functional groups, thus providing an efficient method for the stereoselective synthesis of β-CF3-functionalized acrylamide derivatives. Copyright
Rh-catalyzed asymmetric hydroformylation of functionalized 1,1-disubstituted olefins
Wang, Xiao,Buchwald, Stephen L.
supporting information; experimental part, p. 19080 - 19083 (2012/01/05)
The first method for the highly enantioselective rhodium-catalyzed hydroformylation of 1,1-disubstituted olefins has been developed. By employing either of the P-chirogenic phosphine ligands BenzP* and QuinoxP*, linear aldehydes with β-chirality can be prepared in a highly enantioselective fashion with good chemo- and regioselectivities.
Nitration of α,β-unsaturated esters. Evidence for positive charge build-up adjacent to carbonyl carbon
Hewlins, Stuart A.,Murphy, John A.,Lin, Jian,Hibbs, David E.,Hursthouse, Michael B.
, p. 1559 - 1570 (2007/10/03)
Reactive intermediates formed in the nitration of certain α,β-unsaturated esters with nitronium tetrafluoroborate exhibit behaviour expected of highly reactive α-carbonyl cations. Three diagnostic reaction types have been observed which indicate the presence of these destabilised cations: (i) trapping in a Ritter reaction, (ii) cyclopropane formation from propyl cations, (iii) Wagner-Meerwein migration of alkyl groups. Semi-empirical calculations of the relative gas-phase stabilities of the proposed intermediate cations are useful in rationalising the observed chemistry.
An improved procedure for α-methylenation of lactones
Murta,De Azevedo,Greene
, p. 495 - 503 (2007/10/02)
A variety of γ-butyrolactones, as well as a δ-valerolactone and an ester, have been efficiently converted to their α-methylene derivatives by using an improved decarboxylative methylenation procedure, which is simpler and more general than the previously
