SURF Alum Omar Apolinar receives NSF Graduate Research Fellowship

Congratulations to CSU San Macros senior and former SURF student Omar Apolinar, who has been selected for a 2019 NSF Graduate Research Fellowship. After working for two year with Prof. Robert Iafe at CSUSM, Omar joined the Engle lab last summer as part of the NSF-sponsored SURF program at Scripps Research. Under the mentorship of Mingyu Liu, Omar studied directed catalytic alkene and alkyne functionalization, and his work on asymmetric carbofunctionalization of alkenes was published earlier this year (Angew. Chem. Int. Ed. 2019, 58, 3923). Luckily for us, Omar will return to Scripps Research this fall to begin his Ph.D., and we are all looking forward to welcoming him back. Way to go, Omar! Click here for a link to a full list of awardees.

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pre-print on cascade CuH-catalyzed enantioselective 1,1-aminoborylation of alkynes

Today in a pre-print on ChemRxiv, we describe a highly unique cascade hydrofunctionalization process mediated by a chiral CuH catalyst. This multicomponent reaction transforms terminal alkynes into enantioenriched 1,1-aminoboronates in a single step, streamlining access to this emerging class of pharmacophores. We present preliminary experimental and computational data that sheds light on the reaction mechanism and origins of selectivity.  Congrats to all of the authors from the Engle lab (De-Wei, Yang, Tian-Zhang, and Xin, Automated Synthesis Facility (Jason and Brittany), and Liu lab at Pittsburgh (Huiling)! Click here for a link to the paper.

Van wins IPMI Bright Futures Award Sponsored by Gero Family Trust

Huge congrats to G3 student Van Tran, who has been selected for the International Precious Metals Institute (IPMI) Bright Futures Award sponsored by the Gero Family Trust. The award recognizes Van’s research on the topic of palladium(II)-catalyzed C–C and C–heteroatom bond activation via β-X elimination. More information about IPMI and its student award programs can be found online at: https://www.ipmi.org/page/AwardPrograms. Way to go, Van!

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BT(S) Directing Group Preprint Online

In a pre-print appearing online today in ChemRxiv, Andrew, Kin, and Malkanthi describe the discovery and development of a benzothiazole sulfide, BT(S), directing group for use in catalytic alkene and C–H functionalization reactions catalyzed by palladium(II). The weakly coordinating nature of BT(S) makes it well-suited for reactions that rely on the directing group for selectivity control but also require conformational flexibility in key steps, such as the regioselective oxidative Heck arylation of 1,2-dialkylalkenes. The precursor compound, mercaptobenzothiazole is incredibly cheap (~$50/kg from MilliporeSigma), and the BT(S) can readily be converted to a BT sulfone for Julia olefination chemistry, among other transformations. Congrats to all of the authors, and thanks to Dr. Jason Chen from the Automated Synthesis Facility for guidance on Design of Experiment (DoE) optimization and kinetics runs. Click here for a link to the paper.

2019 Organometallics Class Kicks Off Today

The latest installment of the Scripps Research Organometallics Class (Chem 530) kicks off today! This class will be held on Mondays and Wednesdays, 10:00–11:30 AM, in the Keck Auditorium in the BCC building at Scripps. Like many Scripps courses, this class is open to anyone (in- or outside of Scripps) who is eager to learn more about this topic. If you are interested in attending and are not registered for the class, please contact keary@scripps.edu for more details. You can also follow along remotely! For the first time, all course materials, including video recording of lectures, will be freely available online: https://englelab.com/resources/

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Enantioselective anti-Carboboration of Alkenyl Amides – Now In Press

Over the past two years our lab and other labs around the world have been working hard to develop strategies for controlling enantioselectivity in palladium-catalyzed directed hydrofunctionalization and 1,2-difunctionalization reactions. Last month, we described a Pd(II)/chiral phosphoric acid system for enantioselective hydrofunctionalization with prochiral nucleophiles (click here). In a manuscript appearing online today in ACS Catalysis, we describe a new method for enantioselective anti-carboboration, representing the first time that a 1,2-difunctionalization within this family of reactions has been rendered enantioselectivity (click here). We also propose a new mechanistic model based on stoichiometric experiments to account for the stereoconvergent nature of the transformation. Congrats to all of the authors, Zhen, Xiaohan, and Tian (May). Special props to our two undergrad co-authors, Xiaohan and May! In case anyone missed it, a pre-print of this work was published on ChemRxiv back in early January (click here).

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