Joseph Salamoun Current Literature 11/21/15 Wipf Group
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1 Joseph Salamoun Current Literature 11/21/15 Wipf Group Joe Wipf Group Page 1 of 16 12/29/2015
2 The mechanism of the oxidative addition-transmetallation-reductive elimination process is very complex and the exact details depend on solvents, ligands, the transition metals, and additives. From Transition Metals in the Synthesis of Complex Organic Joe Salamoun Wipf Group by Hegedus L. S. and Page Söderberg 2 of 16 B. C. G., 3 rd ed., /29/2015
3 Nickel Palladium -1, 0, +1, +2, +3, +4 0, +1, +2, +3, +4 Smaller atomic radius Larger atomic radius Less electronegative More electronegative Harder Softer Facile oxidative addition Facile reductive elimination Facile -migratory insertion Facile -hydride elimination Radical pathways more accessible Less expensive Joe Wipf Group Page 3 of 16 12/29/2015 Review: Nature 2014, 509, 299.
4 Reviews: Nature 2014, 509, 299. Joe Wipf Group Page 4 of 16 Eur. J. Org. Chem 12/29/ , 19.
5 From the Garg group: J. Am. Chem. Soc. 2009, 131, J. Am. Chem. Soc. 2011, 133, From the Garg group: Nature 2015, 524, 79. Reviews: Nature 2014, 509, 299. Joe Wipf Group Page 5 of 16 Eur. J. Org. Chem 12/29/ , 19.
6 entry boron source Ni(cod) 2 (mol%) SIPr (mol%) H 2 O (equiv) Yield * 1 5a 6a % 2 5b 6a % 3 5b 6b % 4 5b 6b >99% 5 5b 6b >99% Yields determined by 1 H NMR. More details on screening in SI. Joe Wipf Group Page 6 of 16 12/29/2015 DOI: /NCHEM.2388
7 Joe Wipf * Yields determined by 1 Group Page 7 of 16 12/29/2015 H NMR. Screening for functional group compatibility in SI. DOI: /NCHEM.2388
8 Joe Wipf Group Page 8 of 16 12/29/2015 DOI: /NCHEM.2388
9 Chem. Commun. 2015, 51, Org. Lett. 2015, 17, Chem. Commun. 2014, 50, Org. Lett. 2011, 13, J. Org. Chem. 2012, 77, Joe Wipf Group Page 9 of 16 12/29/2015 Org. Lett. 2006, 8, 5073.
10 New application of nickel catalysis with potential for great utility, especially in med chem. Amides are relatively stable and widely accessible. Very good yields (but by NMR and most purifications by prep TLC) Limited scope (only aromatic amides). Synthetic advantage over traditional acylations not clear. Future Outlook: If the Garg group can demonstrate the coupling of aliphatic amides with chiral aliphatic boronic esters, then this methodology could have a major impact. Joe Wipf Group Page 10 of 16 12/29/2015
11 Gibbs free energy profile of Ni-catalyzed Suzuki Miyaura cross-coupling reaction of phenyl N,N-dimethyl O-carbamate 15 with phenylboronic acid. PCy3 was used as ligand in the calculations. For clarity, the cyclohexyl groups on the ligand are not shown. Published in: Kyle W. Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L. Silberstein; Anna Komaromi; Tom Blackburn; Stephen D. Ramgren; K. N. Houk; Victor Snieckus; Neil K. Garg; J. Am. Chem. Soc. 2011, 133, Joe DOI: Salamoun Wipf Group Page 11 of 16 12/29/2015 Copyright 2011 American Chemical Society
12 Gibbs free energy profile of the Ni-catalyzed Suzuki Miyaura cross-coupling reaction of N,N-dimethyl phenyl O-sulfamate with phenylboronic acid. PCy3 was used as ligand in the calculations. For clarity, the cyclohexyl groups on the ligand are not shown. Published in: Kyle W. Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L. Silberstein; Anna Komaromi; Tom Blackburn; Stephen D. Ramgren; K. N. Houk; Victor Snieckus; Neil K. Garg; J. Am. Chem. Soc. 2011, 133, Joe DOI: Salamoun Wipf Group Page 12 of 16 12/29/2015 Copyright 2011 American Chemical Society
13 Transition-state structures of Ni-catalyzed oxidative additions of (a) N,N-dimethyl phenyl O-carbamate and (b) N,N-dimethyl phenyl O-sulfamate. PCy3 was used as ligand in the calculations. For clarity, the cyclohexyl groups on the ligand are not shown. Published in: Kyle W. Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L. Silberstein; Anna Komaromi; Tom Blackburn; Stephen D. Ramgren; K. N. Houk; Victor Snieckus; Neil K. Garg; J. Am. Chem. Soc. 2011, 133, Joe DOI: Salamoun Wipf Group Page 13 of 16 12/29/2015 Copyright 2011 American Chemical Society
14 Computational study of catalytic cycle. L Hie et al. Nature 524, (2015) doi: /nature14615 Joe Wipf Group Page 14 of 16 12/29/2015
15 In the SI of L Hie et al. Nature 524, (2015) doi: /nature14615 Joe Wipf Group Page 15 of 16 12/29/2015
16 Possible catalytic cycle. Published in: Alan H. Cherney; Nathaniel T. Kadunce; Sarah E. Reisman; J. Am. Chem. Soc. 2013, 135, Joe DOI: Salamoun Wipf Group Page 16 of 16 12/29/2015 Copyright 2013 American Chemical Society
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