Practical method for preparing N-alkyl phosphinic (thio)amides via transfer hydrogenation

Today, Tanner and Zi-Yang (Nick) report a simple and practical method for N-alkylation of phosphinic (thio)amides using primary and secondary alcohols as the alkylating agents. The reaction is compatible with a wide variety of functional groups and employs a commercially available catalyst, Ru-MACHO, which was kindly donated to our lab from Takasago for the purposes of this study. Congrats to both authors, and special props to undergraduate co-first-author, Nick. This paper, which is now available online in Tetrahedron, is part of a special series celebrating Ryan Shenvi’s 2019 Tetrahedron Young Investigator Award. Click here for a link to the paper.

transfer

Former Undergrad Tim Gallagher Receives Fulbright Fellowship

Congratulations to Claremont McKenna College senior Tim Gallagher, who has been selected for a Fulbright Fellowship to Germany! Tim joined the Engle lab at Scripps Research during the summer after his junior year (2018), following two years of research experience in the group of Prof. Anna Wenzel at CMC. In the Engle lab, Tim worked under the mentorship of Van Tran studying new conjunctive cross-coupling reactions with nickel, which then became the subject of his senior thesis at CMC. As a Fulbright Fellow, Tim will spend the next academic year in Münster, Germany, where he will carry out research on arene hydrogenation in the laboratory of Prof. Frank Glorius at WWU Münster. We can’t wait to see photos of your time in Germany. Way to go, Tim!

IMG_4780

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.

omar-apolinar-ar-039-519374

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!

received_2312823255445473

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.