Editorial pubs.acs.org/OPRD
In the Limelight: Carbon−Heteroatom Coupling Chemistry and C−C couplings as an endgame strategy; and finally, Shieh et al. (Novartis, East Hanover, New Jersey, United States) report on a Buchwald−Hartwig amination protocol to achieve a drug substance displaying chirality in the form of atropisomerism. Continuing the stream of C−N bond formation, Merritt and colleagues (Eli Lilly, Indianapolis, IN, United States, and Cork, Ireland) focus on modeling and PAT (process analytical technology) as elements in the design of catalytic aminations. In the field of C−S coupling, Bhaumik et al. (Indian Association for the Cultivation of Science, Jadavpur, India), joining forces with the Nanyang Technological University, Singapore, show how a Cu-grafted mesoporous heterogeneous catalyst is applied in a three-component reaction, and Singer et al. (Pfizer, Groton, CT, United States) employ a late-stage C−S coupling for the synthesis of axitinib. Please enjoy reading these outstanding articles covering a field that has undergone intense development and that is bound to continue following this path for years to come!
hen the Editorial Advisory Board of Organic Process Research & Development (OPRD) meets, there is always a lively debate about what suitable topics to present to the readership in the format of a Special Feature Sectiona unique way of disseminating scientific papers collated under a specific and common headline. In this context, an area that has been seen as one of the highest priorities and deserving of attention and focus is coupling chemistry entailing the formation of bond motifs such as C−C, C−N, C−O, and C−S, due to the demonstrated broad range of applications with proven synthetic utilities over the past decade. It was against this backdrop that we formed a small team of Guest Editors with the pronounced mission of enabling the compilation of the highest-quality papers from renowned scientistsacademic as well as industrialand who would be in a position to deliver insightful accounts of recent developments in carbon−heteroatom couplings with a promise to raise the expectations and attract the interest of the wide and diverse readership of OPRD. It is with the feeling of pride that we herewith offer you the outcome of our endeavors. A total of 10 high-class articles spanning an array of subjects that in their totality show both the versatility of this technology and new developments to further expand beyond the current boundaries. Given the increasingly competitive landscape that defines the publishing arena of today, we want to express our sincere gratitude to all authors who have accepted our call and committed time and energy to deliver manuscripts of high standing and excellent science. Indeed, we are very pleased to present to you papers covering C−X coupling chemistry in its entire breadth, with the exception of C−O bond formation, where the reason for our “failure” is not entirely clear but could, eventually, be explained by a relative scarcity due to this transformation being an, as yet, under-utilized synthetic opportunity. Organ and co-workers (York University, Toronto, Canada) in collaboration with The Dow Chemical Company, Collegeville, PA, United States, lead us off with a review on C−heteroatom couplings using a particular set of Pd complexes. With the stage thus set, there follows a set of articles addressing the most common coupling to be reported, the creation of a C−N linkage where the breadth of nitrogen nucleophiles spans anilines, amides, sulfonamides, and heterocyclic amines. Here you will find a selection of splendid case stories, frequently with a scale-up profile attached, such as those from Kallemeyn and colleagues (AbbVie, North Chicago, IL, United States) on the synthesis of a pyridazinone and from Zhao and co-workers (Sunovion Pharmaceuticals, Marlborough, MA, United States) on a Cumediated amination protocol. Furthermore, Houpis (Janssen Pharmaceutica, Beerse, Belgium) together with WuxiApptec, Shanghai, P.R. China, continues on the theme of using copper catalysis to effect a selective arylation of a sulfonamide in the presence of an amide as part of synthesizing HIV inhibitors. Chung and colleagues (Merck, Rahway, NJ, and Boston, MA, United States) discuss regioselective C−N cross-couplings as part of the asymmetric synthesis of niraparib; Hong and coworkers (Roche, Palo Alto, CA, United States) present C−N
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© 2014 American Chemical Society
Ashok V. Bhatia Process Chemistry, AbbVie, North Chicago, Illinois 60064, United States
Hans-Jürgen Federsel*
Pharmaceutical Development, AstraZeneca, Macclesfield, Cheshire, SK10 2NA U.K.
Qinghao Chen
■
Process Chemistry, Merck & Co., Inc., Rahway, New Jersey 07065, United States
AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected] Notes
Views expressed in this editorial are those of the author and not necessarily the views of the ACS.
Special Issue: Transition Metal-Mediated Carbon-Heteroatom Coupling Reactions Published: January 3, 2014 179
dx.doi.org/10.1021/op400356t | Org. Process Res. Dev. 2014, 18, 179−179
