37742-99-7Relevant articles and documents
Different Selectivities in the Insertions into C(sp2)?H Bonds: Benzofulvenes by Dual Gold Catalysis Competition Experiments
Plajer, Alex J.,Ahrens, Lukas,Wieteck, Marcel,Lustosa, Danilo M.,Babaahmadi, Rasool,Yates, Brian,Ariafard, Alireza,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 10766 - 10772 (2018/08/03)
An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)?H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C?H positions. A bidirectional synthesis with two competing ortho-aryl C?H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C?H bonds with a benzylic methyl group also showed perfect selectivity.
Dual gold catalysis: Synthesis of polycyclic compounds via C-H insertion of gold vinylidenes
Wieteck, Marcel,Tokimizu, Yusuke,Rudolph, Matthias,Rominger, Frank,Ohno, Hiroaki,Fujii, Nobutaka,Hashmi, A. Stephen K.
, p. 16331 - 16336 (2015/01/09)
New and interesting polycyclic compounds have been synthesized from non-conjugated diyne systems by dual gold catalysis. A quaternary carbon center in the backbone and the accompanying Thorpe-Ingold effect enabled the unprecedented insertion of sp3 and sp2 C-H bonds that for the first time were incorporated within the backbone of the diyne system and allowed the construction of complex polycyclic carbon scaffolds inaccessible by previous approaches in which the C-H bonds for the insertion were situated at the other end of the alkyne.
Process development and optimization for production of a potassium ion channel blocker, ICA-17043
Mobele, Bingidimi I.,Venkatraman, Sripathy,McNaughton-Smith, Grant,Gibb, Cameron,Ulysse, Luckner G.,Lindmark, Carl A.,Shaw, Stephen,Marron, Brian,Spear, Kerry,Suto, Mark J.
, p. 1385 - 1392 (2012/11/07)
A scalable process for the manufacture of a potassium ion channel blocker was developed and optimized. Key features of the process include an optimized Grignard reaction, a direct cyanation of the intermediate trityl alcohol derivative, and an improved nitrile hydrolysis protocol, relative to the original acidic hydrolysis conditions, to generate the crude active pharmaceutical ingredient (API) with >95% HPLC purity. The Grignard and the cyanation reactions could be telescoped, resulting in an improved throughput compared to the original four-step process. An effective recrystallization of the API was also developed and the process scaled up to manufacture multiple batches at the pilot scale.