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Dr Robert Phipps

Royal Society University Research Fellow

The assembly of molecules for all manner of applications is occurring constantly – right from novel molecules on a milligram scale to established ones on a tonne scale. The principles and methods employed to achieve this form the basis of synthetic chemistry. Synthetic chemists generally work within established guidelines of reactivity and selectivity which define how we approach the disconnection of a target molecule into smaller building blocks. Establishing new bond disconnections and finding innovative ways to exert control on reaction selectivity is key to advancing synthetic chemistry and thereby streamlining the process of putting together target molecules.

Our research focuses on exploring novel approaches to catalysis for the rapid and efficient construction of small molecules. Of great importance is that the methods are highly selective, which covers chemoselectivity, regioselectivity and enantioselectivity. We are particularly interested in exploring new designs of multifunctional catalysts, which could be purely organic or incorporating transition metals, to facilitate such reactions. Non-covalent interactions such as hydrogen bonds and ion pairs have been shown over the last decade to be powerful tools to apply to chemical catalysis and harnessing these to achieve selectivity plays an important role in our research. We are also very much interested in exploring the potential of other non-covalent interactions for catalysis. 

Background: Robert received his MSci in Chemistry from Imperial College London in 2006. He moved to the University of Cambridge to complete his PhD (2010) with Prof. Matthew Gaunt on the development of new copper-catalysed arylation reactions. In 2011, he moved to the Unviversity of California, Berkeley on a Marie Curie Postdoctoral Fellowship with Prof. F. Dean Toste in the area of asymmetric fluorination using chiral phosphoric acid catalysts. In 2013 he returned to Cambridge for the return year of his Marie Curie Fellowship before taking up his current position as a Royal Society University Research Fellow in October 2014.

Publications

1.         Mihai, M. T.; Phipps, R. J.* Ion-Pair-Directed meta-Selective C–H Borylation of Aromatic Quaternary Ammonium Salts (Synpacts Account) Synlett 2017 DOI: 10.1055/s-0036-1588709

2.         Davis, H. J.; Phipps, R. J.* Harnessing Non‐Covalent Interactions to Exert Control Over Regioselectivity and Site‐Selectivity in Catalytic Reactions Chem. Sci. 2017, 8, 864-877.

3.         Davis, H. J.; Mihai, M. T.; Phipps, R. J.* Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C–H Borylation of Aromatic Quaternary Ammonium Salts J. Am. Chem. Soc. 2016138, 12759-12762. Click for Link.

4.         Beaud, R.; Phipps, R. J.; Gaunt, M.J. Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines J. Am. Chem. Soc. 2016. 138, 13183-13186. Click for Link.

5.         Phipps, R. J.* Synlett 2016, 27, 1024–1026 (commentary). Click for Link.

6.         Yang, X.; Wu, T.; Phipps, R. J.; Toste F. D. Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions. Chem. Rev. 2015, 115, 826. Click for Link.

7.         Tissot, M.+; Phipps, R.J.+; Lucas, C.+; Leon, R.M.; Pace, R.D.M.; Ngouansavanh, T.; Gaunt, M.J.; Gram-scale enantioselective synthesis of the morphinan alkaloids via an ortho-para oxidative biphenol coupling strategy. Angew. Chem. Int. Ed. 2014, 53, 13498 +(Authors contributed equally). Click for Link

8.         Yang, X.+Phipps, R. J.+; Toste, F. D.; Asymmetric Fluorination of α-Branched Cyclohexanones Enabled by a Combination of Chiral Anion Phase-Transfer Catalysis and Enamine Catalysis using     Protected Amino AcidsJ. Am. Chem. Soc. 2014136, 5225-5528 +(Authors contributed equally). Click for Link.

9.         Wu, J.; Wang, Y.; Drljevic, A.; RauniyarV.; Phipps, R. J.; Toste, F. D. A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes. Proc. Natl. Acad. Sci. USA 2013, 110, 13729-13733. Click for Link.

10.         Phipps, R. J.; Toste, F. D. Chiral anion phase-transfer catalysis applied to the direct enantioselective fluorinative dearomatization of phenols J. Am. Chem. Soc. 2013, 135, 1268-1271. Click for Link.

11.         Honjo, T.; Phipps, R. J.; Rauniyar, V.; Toste, F. D. A doubly axially chiral phosphoric acid catalyst for the asymmetric tandem oxyfluorination of enamides. Angew. Chem. Int. Ed. 2012, 51, 9684-9688. Click for Link.

12.         Phipps, R. J.; Hamilton, G. L.; Toste, F. D. The progression of chiral anions from concepts to applications in asymmetric catalysis. Nature Chem. 2012, 4, 603-614. Click for Link

13.         Phipps, R. J.; McMurray, L. M.; Duong, H. A.; Ritter, S.; Gaunt, M. J. Copper-catalyzed alkene arylation with diaryliodonium salts. J. Am. Chem. Soc. 2012, 134, 10773-10776. Click for Link.

14.         Phipps, R. J.; Hiramatsu, K.; Toste, F. D. Asymmetric fluorination of enamides: access to α-fluoroimines using an anionic chiral phase-transfer catalyst J. Am. Chem. Soc. 2012, 134, 8376-8379.Click for Link.

15.         Paddock, V.L.; Phipps, R. J.; Conde-Angulo, A.; Blanco-Martin, A.; Giró-Mañas, C.; Martin, L. J.; White, A. J. P.; Spivey, A. C. (±)-trans,cis-4-Hydroxy-5,6-di-O-isopropylidenecyclohex-2-ene-1-one: synthesis and facile dimerization to decahydrodibenzofurans. J. Org. Chem. 201176, 1483-1486. Click for Link.

16.         Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds. Angew. Chem. Int. Ed. 2011, 50, 463-466. Click for Link.

17.        Ciana, C. L.; Phipps, R. J.; Brandt, J. R.; Magnus, F. –M.; Gaunt, M. J. A highly para-selective copper(II)-catalyzed direct arylation of aniline and phenol derivatives. Angew. Chem. Int. Ed. 201150, 458-462. Click for Link.

18.        Phipps, R. J.; Gaunt, M. J. A meta-selective copper-catalyzed C-H bond arylation. Science 2009, 323, 1593-1597. Click for Link.          

19.        Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions. J. Am. Chem. Soc. 2008130, 8172-8174.Click for Link.  

 

Research Group

Research Interest Group

Telephone number

01223 336367

Email address

rjp71@cam.ac.uk