Chapter 37 — Further Reading

Textbooks

• Hartwig, J. F. (2010). Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books. The standard graduate textbook on organometallic catalysis.

• Crabtree, R. H. (2014). The Organometallic Chemistry of the Transition Metals, 6th ed. Wiley. Excellent introductory text; clear treatment of mechanism.

• Negishi, E. (ed.) (2002). Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley. Comprehensive reference for Pd-catalyzed reactions.

• Tsuji, J. (2005). Palladium Reagents and Catalysts: Innovations in Organic Synthesis. Wiley. Practical perspective on Pd chemistry.

• Astruc, D. (2007). Organometallic Chemistry and Catalysis. Springer. Modern overview.

Primary literature: Pd cross-coupling

• Mizoroki, T., et al. (1971). The Heck reaction (initial discovery). Bulletin of the Chemical Society of Japan 44, 581. Heck Nobel 2010.

• Heck, R. F. (1968). Series of papers on Pd-catalyzed alkene coupling. Journal of the American Chemical Society.

• Suzuki, A. (1981). The Suzuki coupling. Various papers in Synth. Commun. and elsewhere. Nobel 2010.

• Negishi, E., et al. (1977). The Negishi coupling (organozinc). Nobel 2010.

• Stille, J. K. (1986). The Stille coupling (organotin). Angewandte Chemie 25, 508-524.

• Sonogashira, K., et al. (1975). The Sonogashira coupling. Tetrahedron Letters 16(50), 4467-4470.

• Hartwig, J. F. (2008). Pd-catalyzed amination (review). Accounts of Chemical Research 41(11), 1534-1544.

• Buchwald, S. L., et al. (1990s+). Various Buchwald-Hartwig amination papers.

Primary literature: Olefin metathesis

• Chauvin, Y., and Hérisson, J. L. (1971). The Chauvin mechanism. Die Makromolekulare Chemie 141, 161-176. Nobel 2005.

• Schrock, R. R. (1980-1990s). Mo and W carbene catalysts. Various papers in Journal of the American Chemical Society. Nobel 2005.

• Grubbs, R. H. (1992-2000s). Ru carbene catalysts (1st and 2nd generation). Various papers. Nobel 2005.

• Sanford, M. S., et al. (2001). Mechanism of Grubbs catalyst. Journal of the American Chemical Society 123(27), 6543-6554.

• Hoveyda, A. H., et al. (2007). Hoveyda-Grubbs catalyst. Journal of the American Chemical Society 129(7), 1862-1863.

Primary literature: polymerization

• Ziegler, K., and Natta, G. (1955-1957). Various papers on Ziegler-Natta polymerization. Nobel 1963.

• Brookhart, M., et al. (1995). Late-transition-metal polymerization catalysts. Journal of the American Chemical Society.

• Coates, G. W. (2000). Stereo- and tactic control in polymerization. Chemical Reviews 100(4), 1223-1252.

Primary literature: asymmetric catalysis

• Knowles, W. S. (2002). Asymmetric hydrogenation. Nobel Lecture. Angewandte Chemie 41(12). The L-DOPA synthesis.

• Noyori, R. (2002). Asymmetric hydrogenation. Nobel Lecture. Angewandte Chemie 41(12). Ru/BINAP.

• Burk, M. J., et al. (1990s). DuPHOS for asymmetric hydrogenation. Journal of the American Chemical Society.

• Sharpless, K. B. (2002). Asymmetric oxidations. Nobel Lecture. Angewandte Chemie 41(12).

Primary literature: C-H activation

• Bergman, R. G., et al. (multiple papers). Pioneering C-H activation studies (1970s-1980s).

• Hartwig, J. F. (2012). Iridium-catalyzed C-H borylation. Chemical Reviews 112(7), 3759-3795.

• Yu, J.-Q., et al. (multiple papers). Pd-catalyzed C-H activation with directing groups.

• Engle, K. M., et al. (2012). Late-stage C-H activation. Angewandte Chemie 51(5), 1052-1098. Review.

Industrial applications

• Caron, S., et al. (eds.) (2011). Practical Synthetic Organic Chemistry. Wiley. Industrial-scale Pd chemistry.

• Magano, J., and Dunetz, J. R. (2011). "Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals." Chemical Reviews 111(3), 2177-2250.

• Hayler, J. D., et al. (2019). "A pharmaceutical industry perspective on sustainable metal catalysis." Organometallics 38(1), 36-46.

Sitagliptin synthesis

• Hansen, K. B., et al. (2009). The development of the sitagliptin process. Journal of the American Chemical Society 131(25), 8798-8804.

• EPA Presidential Green Chemistry Challenge Award 2006: see https://www.epa.gov/greenchemistry/presidential-green-chemistry-challenge-2006-greener-synthetic-pathways-award.

Computational tools

• Avogadro (https://avogadro.cc/). Visualize Pd cross-coupling intermediates.

• PubChem — look up: sitagliptin (CID 4369359), boceprevir (CID 10324367), Grubbs catalyst (CID 11342334).

• Reaxys for Pd reaction literature.

Online resources

• Master Organic Chemistry, "Pd Cross-Coupling" series. Free undergraduate-level explanations.

• Organometallic Chemistry resources at universities (Yale, MIT, CalTech, etc.).

• Khan Academy: Organic Chemistry — Pd Catalysis. Free videos.

For practice problems

• Klein, David. Organic Chemistry as a Second Language, 4th ed. (Wiley). Limited Pd coverage; supplement with primary literature.

• Karty, Joel. Organic Chemistry: Principles and Mechanisms, 2nd ed. (W. W. Norton, 2018). Decent treatment of Pd cross-coupling.

• Sorrell, Thomas N. Organic Chemistry, 2nd ed. (University Science Books, 2006). Brief Pd coverage.

Mathematically inclined readers

• Hartwig, J. F. (2010). Organotransition Metal Chemistry. Includes computational chemistry of Pd cycles.

• Maron, L., and Eisenstein, O. (2003). DFT analysis of Pd-catalyzed reactions.

Notes on this chapter's pedagogy

Chapter 37 introduces a chemistry that didn't exist when most organic chemistry textbooks were written. Pd cross-coupling and olefin metathesis are 21st-century chemistry — Nobel Prizes were awarded in 2005 and 2010 — but they are now central to industry.

The chapter uses the same mechanism-first approach as the rest of the textbook. The key insight: transition-metal catalysis is mechanism-driven (OA, MI, RE, etc.); the named reactions (Suzuki, Heck, Negishi) are variations on the theme.

Chapter 38 brings together everything in a capstone synthesis chapter — applying all the chemistry of Parts I-VIII to total synthesis of complex molecules.