855749-01-8Relevant academic research and scientific papers
Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds
Lv, Jiahang,Zhao, Binlin,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 691 - 694 (2020/07/13)
Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e
Boron Trichloride-Mediated Synthesis of Indoles via the Aminoboration of Alkynes
Lv, Jiahang,Zhao, Binlin,Liu, Li,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 4054 - 4059 (2018/09/25)
We describe an efficient catalyst- and metal-free aminoboration of alkynes to 3-borylated indoles using one of the least expensive boron sources, BCl3. The major dichloro(indolyl)borane products can be used for the in situ construction of usefu
Aminoboration: Addition of B-N ? Bonds across C-C ?€ Bonds
Chong, Eugene,Blum, Suzanne A.
supporting information, p. 10144 - 10147 (2015/09/01)
This communication demonstrates the first catalytic aminoboration of C-C π bonds by B-N δ bonds and its application to the synthesis of 3-borylated indoles. The regiochemistry and broad functional group compatibility of this addition reaction enable substitution patterns that are incompatible with major competing technologies. This aminoboration reaction effects the formation of C-B and C-N bonds in a single step from aminoboronic esters, which are simple starting materials available on the gram scale. This reaction generates synthetically valuable N-heterocyclic organoboron compounds as potential building blocks for drug discovery. The working mechanistic hypothesis involves a bifunctional Lewis acid/base catalysis strategy involving the combination of a carbophilic gold cation and a trifluoroacetate anion that activate the C-C π bond and the B-N δ bond simultaneously.
Silver-catalyzed cascade cyclization-stannylation of o-alkynylaniline derivatives with 2-tributylstannylfuran: An efficient synthesis of (3-indolyl)stannanes
Liu, Jun,Xie, Xin,Liu, Yuanhong
supporting information, p. 11794 - 11796 (2013/12/04)
A straightforward synthesis of (3-indolyl)stannanes through silver-catalyzed cyclization-stannylation of N-electron-withdrawing group-substituted o-alkynylanilines in the presence of 2-tributylstannylfuran is developed. This method offers several advantages such as no requirement of additional ligands, high efficiency and a wide reaction scope.
Synthesis of carbazoles by dehydro Diels-Alder reactions of ynamides
Martínez-Esperón, M. Fernanda,Rodríguez, David,Castedo, Luis,Saá, Carlos
, p. 3674 - 3686 (2008/09/19)
A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder of ynamides is reported. N-(o-Ethynyl)aryl ynamides and N-(o-ethynyl) arylynamides were prepared in a few steps starting from o-iodoaniline. Thermal c
Coupling and cycloaddition of ynamides: Homo- and Negishi coupling of tosylynamides and intramolecular [4 + 2] cycloaddition of N-(o-ethynyl)phenyl ynamides and arylynamides
Martínez-Esperón, María Fernanda,Rodríguez, David,Castedo, Luis,Saá, Carlos
, p. 3843 - 3855 (2007/10/03)
N,N′-aryl- and N,N′-alkyl-buta-1,3-diyne-1,4-ditosylamides have been synthesized for the first time, in good to excellent yields, by copper-catalyzed dimerization of the corresponding N-aryl or N-alkyl tosylynamides. Negishi coupling of N-ethynylzinc tosy
Synthesis of carbazoles from ynamides by intramolecular dehydro Diels-Alder reactions
Martinez-Esperon, Maria Fernanda,Rodriguez, David,Castedo, Luis,Saa, Carlos
, p. 2213 - 2216 (2007/10/03)
(Chemical Equation Presented) A new approach to carbazoles and benzannulated carbazoles by means of intramolecular dehydro Diels-Alder reactions of ynamides is reported. By using this approach, carbazoles and benzo[b]-, tetrahydrobenzo[b]-, naphtho[1,2-b]
