145782-19-0Relevant articles and documents
Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π-Alkene Activation
Amgoune, Abderrahmane,Bourissou, Didier,Rigoulet, Mathilde,Thillaye du Boullay, Olivier
, p. 16625 - 16630 (2020/07/24)
Heteroarylation of alkenes with aryl iodides was efficiently achieved with a (MeDalphos)AuCl complex through AuI/AuIII catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5-, 6-, and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox/oxidative approaches. In addition, it provides a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols.
TMSOTf mediated '5/6-: Endo-dig ' reductive hydroamination for the stereoselective synthesis of pyrrolidine and piperidine derivatives
Gharpure, Santosh J.,Vishwakarma, Dharmendra S.,Patel, Raj K.
supporting information, p. 6858 - 6861 (2019/06/18)
A TMSOTf mediated 5/6-endo-dig reductive hydroamination cascade on internal alkynylamines gave expedient, stereoselective access to pyrrolidine and piperidine derivatives. We also demonstrate that a protecting group on nitrogen has a profound effect on the reactivity as well as diastereoselectivity of the reductive hydroamination cascade.
NaBArF4-Catalyzed Oxidative Cyclization of 1,5- and 1,6-Diynes: Efficient and Divergent Synthesis of Functionalized γ- and δ-Lactams
Zhu, Bo-Han,Wang, Cai-Ming,Su, Hong-Yu,Ye, Long-Wu
supporting information, p. 58 - 62 (2019/01/04)
An efficient NaBArF4-catalyzed oxidative cyclization of readily available 1,5- and 1,6-diynes has been developed. Importantly, this transition metal-free oxidative catalysis proceeds via a presumable Lewis acid-catalyzed SN2’ pathway, which is distinct from the relevant oxidative rhodium and gold catalysis. This method leads to the facile and practical construction of a diverse range of synthetically useful γ- and δ-lactams in mostly good to excellent yields with broad substrate scope.
Regio- and chemoselective n-1 acylation of indoles: Pd-catalyzed domino cyclization to afford 1,2-fused tricyclic indole scaffolds
Liu, Yongxian,Huang, Yuanqiong,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
, p. 5337 - 5340 (2015/03/30)
A concise method for the synthesis of 1,2-fused tricyclic indole scaffolds by domino cyclization involving a Pd-catalyzed Sonogashira coupling, indole cyclization, regio- and chemoselective N-1 acylation, and 1,4-Michael addition is reported. This method
Synthesis of fused bicyclic aminals through sequential gold/Lewis acid catalysis
Wang, Xi'Anghua,Yao, Zhili,Dong, Shuli,Wei, Fang,Wang, Hong,Xu, Zhenghu
supporting information, p. 2234 - 2237 (2013/06/27)
A novel sequential catalysis by combining gold catalysis with early transition metal catalysis was developed. Biologically important bicyclo[4.n.0] aminals were obtained under very mild conditions.
Reductive cyclization of bromoenynamides with alcohols as hydride source: Synthesis and reactions of 2-amidodienes
Greenaway, Rebecca L.,Campbell, Craig D.,Chapman, Helen A.,Anderson, Edward A.
supporting information, p. 3187 - 3194 (2013/01/15)
Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi- and tricyclic azacycles, which can be further oxidized to the aromatic azacycles. Copyright
Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines
Garcia, Pierre,Evanno, Yannick,George, Pascal,Sevrin, Mireille,Ricci, Gino,Malacria, Max,Auber, C. Torinne,Gandon, Vincent
, p. 2030 - 2033 (2011/06/23)
Bimolecular cobalt-catalyzed [2+2+2] cycloadditions between yne-ynamides and nitriles afford bicyclic 3- or 4-aminopyridines in up to 100% yield. The high regioselectivity observed depends on the substitution pattern at the starting ynamide. Aminopyridines bearing TMS and Ts groups are efficiently deprotected in an orthogonal fashion.
Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
Simonneau, Antoine,Garcia, Pierre,Goddard, Jean-Philippe,Mouries-Mansuy, Virginie,Malacria, Max,Fensterbank, Louis
, p. 1379 - 1386 (2011/11/07)
We herein report the synthesis of 3-fluoro-2-methylene-pyrrolidine (3a) and -piperidine (3b) from 1,5- and 1,6-aminoalkynes, respectively, using a combination of a gold-catalyzed hydroamination reaction followed by electrophilic trapping of an intermediat
Asymmetric allylic alkylation in combination with ring-closing metathesis for the preparation of chiral N-heterocycles
Teichert, Johannes F.,Zhang, Suyan,Van Zijl, Anthoni W.,Slaa, Jan Willem,Minnaard, Adriaan J.,Feringa, Ben L.
supporting information; experimental part, p. 4658 - 4660 (2010/12/19)
Asymmetric copper-catalyzed allylic substitution with methylmagnesium bromide is employed in combination with ring-closing olefin metathesis or ene - yne metathesis to achieve the synthesis of chiral, unsaturated nitrogen heterocycles. The resulting six-
A ruthenium-catalyzed, atom-economical synthesis of nitrogen heterocycles
Trost, Barry M.,Maulide, Nuno,Livingston, Robert C.
supporting information; experimental part, p. 16502 - 16503 (2009/04/13)
The Ruthenium catalyzed, atom-economical domino redox isomerization/cyclization of tethered aminopropargyl alcohols is reported. This process displays a broad scope and functional group tolerance. Furthermore, it presents a novel retrosynthetic disconnect
