Chapter 1
(1) O’Hagan, D. Chem. Soc. Rev. 2008, 37, 308–319.
(2) For selective reviews of acyl fluorides, see: (a) Ogiwara, Y.; Sakai, N. Angew. Chem., Int. Ed. 2020, 59, 574–594; Angew. Chem. 2020, 132, 584–605. (b) Zhao, Q.; Szostak, M. ChemSusChem 2019, 12, 2983–2987. (c) Wang, Z.; Wang, X.; Nishihara, Y. Chem Asian J. 2020, 15, 1234–1247.
(3) For selective highlights of acyl fluorides, see: Blanchard, N.; Bizet, V. Angew. Chem., Int. Ed. 2019, 58, 6814–6817; Angew. Chem. 2019, 131, 6886–6889.
(4) For selected examples on hydrolysis: (a) Swain, C. G.; Scott, C. B. J. Am. Chem. Soc. 1953, 75, 246–248. (b) Satchell, D. P. N. J. Chem. Soc. 1963, 555–557. (c) Bunton, C. A.; Fendler, J. H. J. Org. Chem. 1966, 31, 2307–2312. (d) Motie, R. E.; Satchell, D. P. N.; Wassef, W. N. J. Chem. Soc., Perkin Trans. 2, 1993, 1087–1090. (e) George, C.; Saison, J. Y.; Ponche, J. L.; Mirabel, P. J. Phys. Chem. 1994, 98, 10857–10862.
(5) For selected examples on esterification, see: (a) Pospíšil, J.; Müller, C.; Fürstner, A. Chem. Eur. J. 2009, 15, 5956–5968. (b) Okazoe, T.; Shirakawa, D.; Murata, K. Appl. Sci. 2012, 2, 327–341. (c) Hirai, G.; Nishizawa, E.; Kakumoto, D.; Morita, M.; Okada, M.; Hashizume, D.; Nagashima, S. Sodeoka, M. Chem. Lett. 2015, 44, 1389–1391. (d) Wu, H.; Guo, W.; Daniel, S.; Li, Y.; Liu, C.; Zeng, Z. Chem. Eur. J. 2018, 24, 3444–3447. (e) Craig, R.; Litvajova, M.; Cronin, S. A.; Connon, S. J. Chem. Commun. 2018, 54, 10108–10111.
(6) For selected reviews on C–N bond formation, see: (a) Carpino, L. A.; Beyermann, M.; Wenschuh, H.; Bienert, M. Acc. Chem. Res. 1996, 29, 268–274. (b) Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827–10852. (c) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606–631. (d) El-Faham, A.; Khattab, S. N. Synlett 2009, 886–904. (e) El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111, 6557–6602. (f) Prabhu, G.; Narendra, N.; Basavaprabhu; Panduranga, V.; Sureshbabu, V. V. RSC Adv. 2015, 5, 48331–48362.
(7) For selected examples on amidation, see: (a) Schindler, C. S.; Forster, P. M.; Carreira, E. M. Org. Lett. 2010, 12, 4102–4105. (b) Kielland, N.; Vendrell, M.; Lavilla, R.; Chang, Y.-T. Chem. Commun. 2012, 48, 7401–7403. (c) Mittal, N.; Lippert, K. M.; De, C. K.; Klauber, E. G.; Emge, T. J.; Schreiner, P. R.; Seidel, D. J. Am. Chem. Soc. 2015, 137, 5748–5758. (d) Due-Hansen, M. E.; Pandey, S. K.; Christiansen, E.; Andersen, R.; Hansen, S. V. F.; Ulven, T. Org. Biomol. Chem. 2016, 14, 430–433. (e) Zamiri, M.; Grierson, D. S. Synthesis 2017, 49, 571–578. (f) Guo, W.; Huang, J.; Wu, H.; Liu, T.; Luo, Z.; Jian, J.; Zeng, Z. Org. Chem. Front. 2018, 5, 2950–2954.
(8) For selected examples on C–N bond formation of complex molecules, see: (a) Trachsel, A.; de Saint Laumer, J.-Y.; Haefliger, O. P.; Herrmann, A. Chem. Eur. J. 2009, 15, 2846–2860. (b) Sintes, M.; De Moliner, F.; Caballero-Lima, D.; Denning, D. W.; Read, N. D.; Kielland, N.; Vendrell, M.; Lavilla, R. Bioconjugate Chem. 2016, 27, 1430–1434. (c) Dovgan, I.; Ursuegui, S.; Erb, S.; Michel, C.; Kolodych, S.; Cianférani, S.; Wagner, A. Bioconjugate Chem. 2017, 28, 1452–1457.
(9) For selected examples on synthesis of acyl fluorides, see: (a) Gonay, M.; Batisse, C.; Paquin, J.-F. Synthesis 2020, DOI: 10.1055/s-0040-1705951. (b) Scattolin, T.; Deckers, K.; Schoenebeck, F. Org. Lett. 2017, 19, 5740–5743. (c) Munoz, S. B.; Dang, H.; IspizuaRodriguez, X.; Mathew, T.; Prakash, G. K. S. Org. Lett. 2019, 21, 16590–1663. (d) Liang, Y.; Zhao, Z.; Shibata, N. Commun. Chem. 2020, 3, 59. (e) Gonay, M.; Batisse, C.; Paquin, J.-F. J. Org. Chem. 2020, 85, 10253–10260. (f) Foth, P. J.; Malig, T. C.; Yu, H.; Bolduc, T. G.; Hein, J. E.; Sammis, G. M. Org. Lett. 2020, 22, 6682–6686.
(10) For a selected example on C–H bond formation of acyl fluorides, see: Braden, R.; Himmler, T. J. Organomet. Chem. 1989, 367, C12–C14.
(11) For selected examples of transition-metal-catalyzed decarbonylative C–B bond formation of acyl fluorides, see: (a) Wang, Z.; Wang, X.; Nishihara, Y. Chem. Commun. 2018, 54, 13969– 13972. (b) Malapit, C. A.; Bour, J. R.; Laursen, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2019, 141, 17322–17330.
(12) For selected examples on C–C bond formation of acyl fluorides, see: (a) Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964–15965. (b) Ogiwara, Y.; Maegawa, Y.; Sakino, D.; Sakai, N. Chem. Lett. 2016, 45, 790–792. (c) Boreux, A.; Indukuri, K.; Gagosz, F.; Riant, O. ACS Catal. 2017, 7, 8200–8204. (d) Ogiwara, Y.; Iino, Y.; Sakai, N. Chem. Eur. J. 2019, 25, 6513–6516. (e) Ueda, Y.; Iwai, T.; Sawamura, M. Chem. Eur. J. 2019, 25, 9410–9414. (f) Pan, F.F.; Guo, P.; Li, C.-L.; Su, P.; Shu, X.-Z. Org. Lett. 2019, 21, 3701–3705. (g) Han, J.; Zhou, W.; Zhang, P.-C.; Wang, H.; Zhang, R.; Wu, H.-H.; Zhang, J. ACS Catal. 2019, 9, 6890–6895. (h) Wang, J.; Hoerrner, M. E.; Watson, M. P.; Weix, D. J. Angew. Chem., Int. Ed. 2020, 59, 13484–13489.
(13) For selected examples on decarbonylative C–C bond formation of acyl fluorides, see: (a) Keaveney, S. T.; Schoenebeck, F. Angew. Chem., Int. Ed. 2018, 57, 4073–4077; Angew. Chem. 2018, 130, 4137–4141. (b) Okuda, Y.; Xu, J.; Ishida, T.; Wang, C.; Nishihara, Y. ACS Omega 2018, 3, 13129–13140. (c) Malapit, C. A.; Bour, J. R.; Brigham, C. E.; Sanford, M. S. Nature 2018, 563, 100–104. (d) Sakurai, S.; Yoshida, T.; Tobisu, M. Chem. Lett. 2019, 48, 94–97. (e) Chen, Q.; Fu, L.; Nishihara Y. Chem. Commun. 2020, 56, 7977–7980. (f) Fu, L.; Chen, Q.; Wang, Z.; Nishihara, Y. Org. Lett. 2020, 22, 2350–2353. (g) Sakurai, S.; Tobisu, M. Chem. Lett. 2021, 50, 151–153.
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(15) For a selected example of decarbonylative C–Si bond formation of acyl fluorides, see: Wang, X.; Wang, Z.; Nishihara, Y. Chem. Commun. 2019, 55, 10507–10510.
(16) For selected examples of transition-metal-catalyzed C–Se bond formation of acyl fluorides, see: Arisawa, M.; Suzuki, R.; Ohashi, K.; Yamaguchi, M. Asian J. Org. Chem. 2020, 9, 553–556.
(17) For selected examples of decarbonylative C–Sn bond formation of acyl fluorides, see: (a) Wang, X.; Wang, Z.; Liu, L.; Asanuma, Y.; Nishihara, Y. Molecules 2019, 24, 1671–1681. (b) Kayumov, M.; Zhao, J.-N.; Mirzaakhmedov, S.; Wang, D.-Y.; Zhang, A. Adv. Synth. Catal. 2020, 362, 776–781.
(18) Ogiwara, Y.; Sakino, D.; Sakurai, Y.; Sakai, N. Eur. J. Org. Chem. 2017, 4324–4327.
(19) Sakurai, Y.; Ogiwara, Y.; Sakai, N. Chem. Eur. J. 2020, 26, 12972–12977.
(20) Ogiwara, Y.; Sakurai, Y.; Hattori, H.; Sakai, N. Org. Lett. 2018, 20, 4204–4208.
Chapter 2
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Chapter 3
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(34) The crystallographic data for 32 has been deposited at the Cambridge Crystallographic Data Centre under reference number CCDC 1975847 and can be obtained free of charge.
(35) For selected examples of catalytic reactions using aldehydes as the CO source, see: (a) Morimoto, T.; Fuji, K.; Tsutsumi, K.; Kakiuchi, K. J. Am. Chem. Soc. 2002, 124, 3806–3807. (b) Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619–1621. (c) Morimoto, T.; Yamasaki, K.; Hirano, A.; Tsutsumi, K.; Kagawa, N.; Kakiuchi, K.; Harada, Y.; Fukumoto, Y.; Chatani, N.; Nishioka, T. Org. Lett. 2009, 11, 1777–1780. (d) Furusawa, T.; Tanimoto, H.; Nishiyama, Y.; Morimoto, T.; Kakiuchi, K. Adv. Synth. Catal. 2017, 359, 240–245.
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(39) Several mechanistic studies into the origin of the exo-selectivity of addition reactions of norbornene have been reported, and exo-selectivity has been explained by the energetic preference for the formation of an exo π-complex than the analogous endo-isomers, see: (a) Okuda, Y.; Szilagyi, R. K.; Mori, S.; Nishihara, Y. Dalton Trans. 2014, 43, 9537–9548. (b) Ishitsuka, T.; Okuda, Y.; Szilagyi, R. K.; Mori, S.; Nishihara, Y. Dalton Trans. 2016, 45, 7786–7793.
(40) Several mechanisms for the palladation step during the formation of complex E are possible: electrophilic aromatic substitution via a Wheland-type intermediate or a concerted metalationdeprotonation (CMD) mechanism; for details, see: Wang, J.; Dong, G. Chem. Rev. 2019, 119, 7478–7528.
(41) Although a kinetic experiment to calculate Kinetic Isotope Effect (KIE) value was investigated, the experimental results have low reproducibility.
Chapter 4
(42) A representative example of the ligand-directed non-decarbonylative and decarbonylative conversion of acyl chlorides: (a) Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2009, 131, 6668–6669. (b) Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 1268–1274.
(43) (a) A nickel-catalyzed divergent coupling of aromatic esters and alkylboranes was reported very recently. In the presence of PCy 3 as a ligand and Cs2CO3 as a base, non-decarbonylative coupling proceeded to form the ketones, while utilizing DCPE provided the decarbonylative coupling products; see: Chatupheeraphat, A.; Liao, H.-H.; Srimontree, W.; Guo, L.; Minenkov, Y.; Poater, A.; Cavallo, L.; Rueping, M. J. Am. Chem. Soc. 2018, 140, 3724–3735. (b) A relative palladium-catalyzed switchable Suzuki−Miyaura reaction was also developed: Masson-Makdissi, J.; Vandavasi, J. K.; Newman, S. G. Org. Lett. 2018, 20, 4094–4098.
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(46) An example of non-decarbonylative reaction of esters and hydrosilanes: Nakanishi, J.; Tatamidani, H.; Fukumoto, Y.; Chatani, N. Synlett 2006, 2006, 869–872.
(47) Selected examples of non-decarbonylative reaction of acid anhydrides and hydrosilanes: (a) Fujihara, T.; Cong, C.; Terao, J.; Tsuji, Y. Adv. Synth. Catal. 2013, 355, 3420–3424. (b) Fujihara, T.; Hosomi, T.; Cong, C.; Hosoki, T.; Terao, J.; Tsuji, Y. Tetrahedron 2015, 71, 4570–4574.
(48) Selected examples of decarbonylative reaction of carboxylic acid derivatives and hydrosilanes: (a) Bai, X.-F.; Xu, L.-W.; Zheng, L.-S.; iang, J.-X.; Lai, G.-Q.; Shang, J.-Y. Chem.-Eur. J. 2012, 18, 8174–8179. (b) Dey, A.; Sasmal, S.; Seth, K.; Lahiri, G. K.; Maiti, D. ACS Catal. 2017, 7, 433–437. (c) Yue, H.; Guo, L.; Lee, S.-C.; Liu, X.; Rueping, M. Angew. Chem., Int. Ed. 2017, 56, 3972–3976.
(49) For formation of the decarbonylative reaction products 54, another possible mechanism exists via the initial generation of aldehydes 53 and the subsequent formyl C−H bond cleavage and decarbonylation. Thus, aldehyde 53a as a starting substrate was then treated with Et 3SiH and Pd(OAc)2/DCPE, but decarbonylation was not observed. This result indicates that the formyl C−H oxidative addition of 53 is not a major pathway for the production of 54.
(50) Several other mechanisms involving partial dissociation of DCPE are also possible: (a) Hong, X.; Liang, Y.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 2017–2025. (b) Lu, Q.; Yu, H.; Fu, Y. J. Am. Chem. Soc. 2014, 136, 8252–8260. See also ref 43b.
Experimental Section
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