8.1.14.23 Hetaryllithium Compounds (Update 2025)

Abstract

This is an update to the previous Science of Synthesis chapter on aryl- and hetaryllithium compounds (Section 8.1.14). This update is focused solely on hetaryllithium compounds and covers those advances in the preparation and reactivity of lithiated hetarenes described in articles that were published between 2004 and 2023. Reviewed herein are direct deprotonation, halogen –lithium exchange, and directed-metalation strategies to access a diverse range of lithiated nitrogen-, oxygen- or sulfur-based hetarenes. Selected classical strategies to prepare hetaryllithium compounds covered in the previous chapter are also included in this update, since novel applications and further transformations of these hetaryllithium compounds have been explored.

Key words

lithium compounds - lithiation - halogen–lithium exchange - aromatic compounds - hetarenes - metalation - furans - thiophenes - pyrroles - indoles - pyridines - quinolines - imidazoles - oxazoles - thioxazoles - pyrazoles - diazines - heterocycles

• 1 Gribble GW. Science of Synthesis 2006; 8: 357

• 2 Schlosser M. Angew. Chem. Int. Ed. 2005; 44: 376

• 3 Chinchilla R, Nájera C, Yus M. Chem. Rev. 2004; 104: 2667

• 4 Chinchilla R, Nájera C, Yus M. ARKIVOC 2007; x, 152 available online at www.arkat-usa.org

• 5 Sotomayor N, Lete E. Curr. Org. Chem. 2003; 7: 275

• 6 Chevallier F, Mongin F. Chem. Soc. Rev. 2008; 37: 595

• 7 Schlosser M, Mongin F. Chem. Soc. Rev. 2007; 36: 1161

• 8 Pace V, Luisi R. ChemCatChem 2014; 6: 1516

• 9 Mulvey RE, Robertson SD. Angew. Chem. Int. Ed. 2013; 52: 11 470

• 10 Algera RF, Gupta L, Hoepker AC, Liang J, Ma Y, Singh KJ, Collum DB. J. Org. Chem. 2017; 82: 4513

• 11 Snieckus V. Chem. Rev. 1990; 90: 879

• 12 Anctil EJG, Snieckus V. J. Organomet. Chem. 2002; 653: 150

• 13 Board J, Cosman JL, Rantanen T, Singh SP, Snieckus V. Platinum Met. Rev. 2013; 57: 234

• 14 Inoue K, Okano K. Asian J. Org. Chem. 2020; 9: 1548

• 15 Schnürch M, Spina M, Khan AF, Mihovilovic MD, Stanetty P. Chem. Soc. Rev. 2007; 36: 1046

• 16 Erb W, Mongin F. Tetrahedron 2016; 72: 4973

• 17 Yoshida J.-i, Nagaki A, Yamada T. Chem.–Eur. J. 2008; 14: 7450

• 18 Yoshida J.-i, Takahashi Y, Nagaki A. Chem. Commun. (Cambridge) 2013; 49: 9896

• 19 Fanelli F, Parisi G, Degennaro L, Luisi R. Beilstein J. Org. Chem. 2017; 13: 520

• 20 Colella M, Nagaki A, Luisi R. Chem.–Eur. J. 2020; 26: 19

• 21 Senatore R, Malik M, Pace V. Adv. Synth. Catal. 2022; 364: 2890

• 22 Harenberg JH, Weidmann N, Knochel P. Synlett 2020; 31: 1880

• 23 Power M, Alcock E, McGlacken GP. Org. Process Res. Dev. 2020; 24: 1814

• 24 Mulvey RE, Mongin F, Uchiyama M, Kondo Y. Angew. Chem. Int. Ed. 2007; 46: 3802

• 25 Haag B, Mosrin M, Ila H, Malakhov V, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9794

• 26 Robertson SD, Uzelac M, Mulvey RE. Chem. Rev. 2019; 119: 8332

• 27 Gentner TX, Mulvey RE. Angew. Chem. Int. Ed. 2021; 60: 9247

• 28 Kremsmair A, Hess A, Heinz B, Knochel P. Chem.–Eur. J. 2022; 28 e202103269

• 29 Shea KM, In: Palladium in Heterocyclic Chemistry Li JJ, Gribble G. Elsevier Oxford 2007; 26. 303

• 30 Chen J, Lim JW, Ong DY, Chiba S. Chem. Sci. 2022; 13: 99

• 31 Pedrosa R, Sayalero S, Vicente M, Casado B. J. Org. Chem. 2005; 70: 7273

• 32 You W, Li Y, Brown MK. Org. Lett. 2013; 15: 1610

• 33 Liu C, Achtenhagen M, Szostak M. Org. Lett. 2016; 18: 2375

• 34 Gao B, Li S, Wu P, Moses JE, Sharpless KB. Angew. Chem. Int. Ed. 2018; 57: 1939

• 35 Roman BI, Monbaliu J.-C, De Coen LM, Verhasselt S, Schuddinck B, Van Hoeylandt E, Stevens CV. Eur. J. Org. Chem. 2014; 2594

• 36 Takeda N, Kobori Y, Okamura K, Yasui M, Ueda M. Org. Lett. 2020; 22: 9740

• 37 Guisot NES, Ella Obame I, Ireddy P, Nourry A, Saluzzo C, Dujardin G, Dubreuil D, Pipelier M, Guillarme S. J. Org. Chem. 2016; 81: 2364

• 38 Gao F, Lee Y, Mandai K, Hoveyda AH. Angew. Chem. Int. Ed. 2010; 49: 8370

• 39 Pérez-Caaveiro C, Pérez Sestelo J, Martínez MM, Sarandeses LA. J. Org. Chem. 2014; 79: 9586

• 40 Giannerini M, Fañanás-Mastral M, Feringa BL. Nature Chem. 2013; 5: 667

• 41 Hornillos V, Giannerini M, Vila C, Fañanás-Mastral M, Feringa BL. Org. Lett. 2013; 15: 5114

• 42 Vila C, Hornillos V, Giannerini M, Fañanás-Mastral M, Feringa BL. Chem.–Eur. J. 2014; 20: 13 078

• 43 Vila C, Hornillos V, Fañanás-Mastral M, Feringa BL. Org. Biomol. Chem. 2014; 12: 9321

• 44 Bonet A, Odachowski M, Leonori D, Essafi S, Aggarwal VK. Nature Chem. 2014; 6: 584

• 45 Odachowski M, Bonet A, Essafi S, Conti-Ramsden P, Harvey JN, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2016; 138: 9521

• 46 Paul S, Das KK, Manna S, Panda S. Chem.–Eur. J. 2020; 26: 1922

• 47 Bock I, Bornowski H, Ranft A, Theis H. Tetrahedron 1990; 46: 1199

• 48 Boukouvalas J, Loach RP. J. Org. Chem. 2008; 73: 8109

• 49 Lee GCM, Holmes JM, Harcourt DA, Garst ME. J. Org. Chem. 1992; 57: 3126

• 50 Comins DL, Killpack MO. J. Org. Chem. 1987; 52: 104

• 51 Stanetty P, Kolodziejczyk K, Roiban GD, Mihovilovic MD. Synlett 2006; 789

• 52 Kolodziejczyk K, Roiban GD, Schnürch M, Mihovilovic MD, Stanetty P. Monatsh. Chem. 2009; 140: 1349

• 53 Shirke RP, Ramasastry SSV. J. Org. Chem. 2015; 80: 4893

• 54 Korshin EE, Leitus GM, Bendikov M. Org. Biomol. Chem. 2014; 12: 6661

• 55 Tofi M, Georgiou T, Montagnon T, Vassilikogiannakis G. Org. Lett. 2005; 7: 3347

• 56 Ly ND, Schlosser M. Helv. Chim. Acta 1977; 60: 2085

• 57 Carpenter AJ, Chadwick DJ. Tetrahedron 1985; 41: 3803

• 58 Sato N, Yue Q. Tetrahedron 2003; 59: 5831

• 59 Miyagawa N, Murase Y, Okano K, Mori A. Synlett 2017; 28: 1106

• 60 Mari D, Miyagawa N, Okano K, Mori A. J. Org. Chem. 2018; 83: 14 126

• 61 Tilly D, Magolan J, Mortier J. Chem.–Eur. J. 2012; 18: 3804

• 62 Sibi MP, Snieckus V. J. Org. Chem. 1983; 48: 1935

• 63 James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V. J. Org. Chem. 2009; 74: 4094

• 64 Amna B, Siddiqi HM, Hassan A, Ozturk T. RSC Adv. 2020; 10: 4322

• 65 Huang J. Eur. J. Org. Chem. 2021; 5775

• 66 Gilman H, Shirley DA. J. Am. Chem. Soc. 1949; 71: 1870

• 67 Granitzka M, Pöppler A.-C, Schwarze EK, Stern D, Schulz T, John M, Herbst-Irmer R, Pandey SK, Stalke D. J. Am. Chem. Soc. 2012; 134: 1344

• 68 Yang Y, Hammond GB, Umemoto T. Angew. Chem. Int. Ed. 2022; 61 e202211688

• 69 Andresini M, Carret S, Degennaro L, Ciriaco F, Poisson J.-F, Luisi R. Chem.–Eur. J. 2022; 28 e202202066

• 70 Zhang Z.-X, Bell C, Ding M, Willis MC. J. Am. Chem. Soc. 2022; 144: 11 851

• 71 Ghinato S, Territo D, Maranzana A, Capriati V, Blangetti M, Prandi C. Chem.–Eur. J. 2021; 27: 2868

• 72 Fuji K, Tamba S, Shono K, Sugie A, Mori A. J. Am. Chem. Soc. 2013; 135: 12 208

• 73 Jeeva S, Lukoyanova O, Fox A, Dadvand A, Rosei F, Perepichka DF. Adv. Funct. Mater. 2010; 20: 1661

• 74 May L, Daniel S, Müller TJJ. Org. Chem. Front. 2020; 7: 329

• 75 Taylor EC, Vogel DE. J. Org. Chem. 1985; 50: 1002

• 76 Götz G, Scheib S, Klose R, Heinze J, Bäuerle P. Adv. Funct. Mater. 2002; 12: 723

• 77 Smith K, Barratt ML. J. Org. Chem. 2007; 72: 1031

• 78 Klingensmith LM, Bio MM, Moniz GA. Tetrahedron Lett. 2007; 48: 8242

• 79 Klatt T, Werner V, Maximova MG, Didier D, Apeloig Y, Knochel P. Chem.–Eur. J. 2015; 21: 7830

• 80 Luo Y.-L, Du H.-Z, Guan B.-T. Org. Chem. Front. 2021; 8: 4171

• 81 Kano S, Yuasa Y, Yokomatsu T, Shibuya S. Heterocycles 1983; 20: 2035

• 82 Getmanenko YA, Tongwa P, Timofeeva TV, Marder SR. Org. Lett. 2010; 12: 2136

• 83 Okano K, Sunahara K, Yamane Y, Hayashi Y, Mori A. Chem.–Eur. J. 2016; 22: 16 450

• 84 Hayashi Y, Okano K, Mori A. Org. Lett. 2018; 20: 958

• 85 Devarie-Baez NO, Shuhler BJ, Wang H, Xian M. Org. Lett. 2007; 9: 4655

• 86 Levine DR, Siegler MA, Tovar JD. J. Am. Chem. Soc. 2014; 136: 7132

• 87 Saied T, Demangeat C, Panossian A, Leroux FR, Fort Y, Comoy C. Eur. J. Org. Chem. 2019; 5275

• 88 Slocum DW, Koonsvitsky BP. J. Org. Chem. 1976; 41: 3664

• 89 DellaVecchia L, Vlattas I. J. Org. Chem. 1977; 42: 2649

• 90 Doadt EG, Snieckus V. Tetrahedron Lett. 1985; 26: 1149

• 91 Graham SL, Scholz TH. J. Org. Chem. 1991; 56: 4260

• 92 Vendina I, Parkova A, Trapencieris P. Heterocycles 2014; 88: 1565

• 93 Borowska E, Durka K, Luliński S, Serwatowski J, Woźniak K. Eur. J. Org. Chem. 2012; 2208

• 94 Fattuoni C, Usai M, Cabiddu M, Cadoni E, De Montis S, Cabiddu S. Synthesis 2007; 1827

• 95 Shirley DA, Gross BH, Roussel PA. J. Org. Chem. 1955; 20: 225

• 96 Zhao C, Song C. Tetrahedron Lett. 2021; 68: 152 907

• 97 Hasan I, Marinelli ER, Lin L.-CC, Fowler FW, Levy AB. J. Org. Chem. 1981; 46: 157

• 98 Martinez GR, Grieco PA, Srinivasan CV. J. Org. Chem. 1981; 46: 3760

• 99 Gharpure M, Stoller A, Bellamy F, Firnau G, Snieckus V. Synthesis 1991; 1079

• 100 Edwards MP, Ley SV, Lister SG, Palmer BD. J. Chem. Soc., Chem. Commun. 1983; 630

• 101 Liu J.-H, Yang Q.-C, Mak TCW, Wong HNC. J. Org. Chem. 2000; 65: 3587

• 102 Morikawa D, Morii K, Yasuda Y, Mori A, Okano K. J. Org. Chem. 2020; 85: 8603

• 103 Morii K, Yasuda Y, Morikawa D, Mori A, Okano K. J. Org. Chem. 2021; 86: 13 388

• 104 Okumi T, Mori A, Okano K. Chem. Commun. (Cambridge) 2023; 59: 1046

• 105 Morrison MD, Hanthorn JJ, Pratt DA. Org. Lett. 2009; 11: 1051

• 106 Bailey N, Demont E, Garton N, Seow H.-X. Synlett 2008; 185

• 107 Heeran D, Sandford G. Eur. J. Org. Chem. 2019; 2339

• 108 Iwao M, Kuraishi T. Tetrahedron Lett. 1985; 26: 6213

• 109 Groenendaal L, Van Loo ME, Vekemans JAJM, Meijer EW. Synth. Commun. 1995; 25: 1589

• 110 Fukuda T, Ohta T, Sudo E.-i, Iwao M. Org. Lett. 2010; 12: 2734

• 111 Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem. Rev. 2011; 111: 6984

• 112 Grimmett MR, Iddon B. Heterocycles 1994; 37: 2087

• 113 Gérard A.-L, Bouillon A, Mahatsekake C, Collot V, Rault S. Tetrahedron Lett. 2006; 47: 4665

• 114 Beak P, Brown RA. J. Org. Chem. 1982; 47: 34

• 115 Schlosser M, Volle J.-N, Leroux F, Schenk K. Eur. J. Org. Chem. 2002; 2913

• 116 Burns M, Perkins D, Chan LC, Pilling MJ, Jawor-Baczynska A, Mullen AK, Steven A, Wimsey C, Elmekawy A, Lamacraft A, Dobson BC, McMillan AE, Hose DRJ, Inglesby PA, Raw SA, Jones MF. Org. Process Res. Dev. 2021; 25: 858

• 117 Jacob C, Lamberth C. Tetrahedron Lett. 2019; 60: 530

• 118 Ondi L, Schlosser M. Eur. J. Org. Chem. 2006; 2417

• 119 Levchenko V, Dmytriv YV, Tymtsunik AV, Liubchak K, Rudnichenko A, Melnyk AV, Veselovych SY, Borodulin YV, Otsalyuk OM, Tolmachev AA, Mykhailiuk PK. J. Org. Chem. 2018; 83: 3265

• 120 McLaughlin M, Marcantonio K, Chen C.-y, Davies IW. J. Org. Chem. 2008; 73: 4309

• 121 Balle T, Vedsø P, Begtrup M. J. Org. Chem. 1999; 64: 5366

• 122 Browne DL, Taylor JB, Plant A, Harrity JPA. J. Org. Chem. 2010; 75: 984

• 123 Hanamoto T, Egashira M, Ishizuka K, Furuno H, Inanaga J. Tetrahedron 2006; 62: 6332

• 124 Bellina F, Rossi R. Adv. Synth. Catal. 2010; 352: 1223

• 125 Iddon B. Heterocycles 1985; 23: 417

• 126 Iddon B, Ngochindo RI. Heterocycles 1994; 38: 2487

• 127 Chadwick DJ, Ngochindo RI. J. Chem. Soc., Perkin Trans. 1 1984; 481

• 128 Sundberg RJ. J. Heterocycl. Chem. 1977; 14: 517

• 129 Carpenter AJ, Chadwick DJ. Tetrahedron 1986; 42: 2351

• 130 Katritzky AR, Rewcastle GW, Fan WQ. J. Org. Chem. 1988; 53: 5685

• 131 Love BE. J. Org. Chem. 2007; 72: 630

• 132 Lipshutz BH, Huff B, Hagen W. Tetrahedron Lett. 1988; 29: 3411

• 133 Whitten JP, Matthews DP, McCarthy JR. J. Org. Chem. 1986; 51: 1891

• 134 Langhammer I, Erker T. Heterocycles 2005; 65: 2721

• 135 Eriksen BL, Vedsø P, Morel S, Begtrup M. J. Org. Chem. 1998; 63: 12

• 136 Manoharan TS, Brown RS. J. Org. Chem. 1988; 53: 1107

• 137 Laroche C, Kerwin SM. Tetrahedron Lett. 2009; 50: 5194

• 138 Torregrosa R, Pastor IM, Yus M. Tetrahedron 2005; 61: 11 148

• 139 Torregrosa R, Pastor IM, Yus M. ARKIVOC vii, 2008; 8 available online at www.arkat-usa.org/

• 140 Torregrosa R, Pastor IM, Yus M. Tetrahedron 2007; 63: 947

• 141 Martínez R, Torregrosa R, Pastor I, Yus M. Synthesis 2012; 44: 2630

• 142 Do H.-Q, Daugulis O. Org. Lett. 2009; 11: 421

• 143 Katritzky AR, Slawinski JJ, Brunner F, Gorun S. J. Chem. Soc., Perkin Trans. 1 1989; 1139

• 144 Eriksen BL, Vedsø P, Begtrup M. J. Org. Chem. 2001; 66: 8344

• 145 Delest B, Nshimyumukiza P, Fasbender O, Tinant B, Marchand-Brynaert J, Darro F, Robiette R. J. Org. Chem. 2008; 73: 6816

• 146 Rault S, Primas N, Bouillon A, Lancelot J.-C, Santos J, Lohier J.-F. Lett. Org. Chem. 2008; 5: 8

• 147 Wendler T, Schütt C, Näther C, Herges R. J. Org. Chem. 2012; 77: 3284

• 148 Lundevall FJ, Bjørsvik HR. Eur. J. Org. Chem. 2023; 26 e202201504

• 149 Inoue K, Feng Y, Mori A, Okano K. Chem.–Eur. J. 2021; 27: 10 267

• 150 Pirrung MC, Ghorai S, Ibarra-Rivera TR. J. Org. Chem. 2009; 74: 4110

• 151 Atkins JM, Vedejs E. Org. Lett. 2005; 7: 3351

• 152 Flegeau EF, Popkin ME, Greaney MF. Org. Lett. 2008; 10: 2717

• 153 Vedejs E, Luchetta LM. J. Org. Chem. 1999; 64: 1011

• 154 Pandey SK, Guttormsen Y, Haug BE, Hedberg C, Bayer A. Org. Lett. 2015; 17: 122

• 155 Williams DR, Fu L. Org. Lett. 2010; 12: 808

• 156 Wollnitzke P, Essig S, Gölz JP, Von Schwarzenberg K, Menche D. Org. Lett. 2020; 22: 6344

• 157 Wagner R, Wollnitzke P, Essig S, Gölz JP, Menche D. Synthesis 2023; 55: 3927

• 158 Miller RA, Smith RM, Marcune B. J. Org. Chem. 2005; 70: 9074

• 159 Stanetty P, Spina M, Mihovilovic MD. Synlett 2005; 1433

• 160 Schnürch M, Khan AF, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2009; 3228

• 161 Williams DR, Fu L. Synlett 2010; 591

• 162 Proust N, Chellat M, Stambuli J. Synthesis 2011; 3083

• 163 Morita T, Yugandar S, Fuse S, Nakamura H. Tetrahedron Lett. 2018; 59: 1159

• 164 Hu F, Szostak M. Adv. Synth. Catal. 2015; 357: 2583

• 165 Poh J.-S, García-Ruiz C, Zúñiga A, Meroni F, Blakemore DC, Browne DL, Ley SV. Org. Biomol. Chem. 2016; 14: 5983

• 166 Deng S, Taunton J. Org. Lett. 2005; 7: 299

• 167 Kelly TR, Lang F. Tetrahedron Lett. 1995; 36: 9293

• 168 Česnek M, Šafránek M, Dračínský M, Tlouštová E, Mertlíková-Kaiserová H, Hayes MP, Watts VJ, Janeba Z. ChemMedChem 2022; 17 e202100568

• 169 Havel S, Khirsariya P, Akavaram N, Paruch K, Carbain B. J. Org. Chem. 2018; 83: 15 380

• 170 Zambon A, Borsato G, Brussolo S, Frascella P, Lucchini V. Tetrahedron Lett. 2008; 49: 66

• 171 Uzelac EJ, Rasmussen SC. J. Org. Chem. 2017; 82: 5947

• 172 Magata T, Hirokawa Y, Moriguchi Y, Yokoi R, Nojiri S, Miyazaki R, Akasako S, Takahashi R, Nishida M, Hakoda J, Nakayama R, Tanaka A, Maezaki N. Tetrahedron Lett. 2019; 60: 718

• 173 Gill M. Tetrahedron 1984; 40: 621

• 174 Kumar A, Thorat KG, Ravikanth M. Org. Lett. 2018; 20: 4871

• 175 Elmir L, Bentabed-Ababsa G, Erb W, Roisnel T, Mongin F. Eur. J. Org. Chem. 2023; 26 e202300024

• 176 Paris TJ, Schwartz C, Willand-Charnley R. J. Org. Chem. 2021; 86: 2369

• 177 Crich D, Grant D. J. Org. Chem. 2005; 70: 2384

• 178 Sanz R, Castroviejo MP, Fernández Y, Fañanás FJ. J. Org. Chem. 2005; 70: 6548

• 179 Feberero C, Virumbrales C, Sedano C, Renedo L, Suárez-Pantiga S, Sanz R. Molecules 2022; 27: 525

• 180 L’Helgoual’c J.-M, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F. J. Org. Chem. 2008; 73: 177

• 181 Kamila S, Mukherjee C, Mondal SS, De A. Tetrahedron 2003; 59: 1339

• 182 Hansen MM, Clayton MT, Godfrey AG, Grutsch Jr JL, Keast SS, Kohlman DT, McSpadden AR, Pedersen SW, Ward JA, Xu Y.-C. Synlett 2004; 1351

• 183 Djukanovic D, Heinz B, Mandrelli F, Mostarda S, Filipponi P, Martin B, Knochel P. Chem.–Eur. J. 2021; 27: 13 977

• 184 Yang Y, Shi Z. Chem. Commun. (Cambridge) 2018; 54: 1676

• 185 Ila H, Markiewicz J, Malakhov V, Knochel P. Synthesis 2013; 45: 2343

• 186 Shirley DA, Roussel PA. J. Am. Chem. Soc. 1953; 75: 375

• 187 Cutri S, Diez A, Bonin M, Micouin L, Husson H.-P. Org. Lett. 2005; 7: 1911

• 188 Zhang J, Hu Y, Wang H, Guo A, Kong J, Ma R, Wu T, Wang Y, Li L.-S, Mai W, Ren P, Deng X. Org. Process Res. Dev. 2018; 22: 97

• 189 Deeming AS, Russell CJ, Hennessy AJ, Willis MC. Org. Lett. 2014; 16: 150

• 190 Wu J, Yang X, He Z, Mao X, Hatton TA, Jamison TF. Angew. Chem. Int. Ed. 2014; 53: 8416

• 191 Qi T, Qiu W, Liu Y, Zhang H, Gao X, Liu Y, Lu K, Du C, Yu G, Zhu D. J. Org. Chem. 2008; 73: 4638

• 192 Yang Z.-K, Wang D.-Y, Minami H, Ogawa H, Ozaki T, Saito T, Miyamoto K, Wang C, Uchiyama M. Chem.–Eur. J. 2016; 22: 15 693

• 193 Shigeno M, Tohara I, Nozawa-Kumada K, Kondo Y. Eur. J. Org. Chem. 2020; 1987

• 194 Sundberg RJ, Russell HF. J. Org. Chem. 1973; 38: 3324

• 195 Sundberg RJ, Parton RL. J. Org. Chem. 1976; 41: 163

• 196 Saulnier MG, Gribble GW. J. Org. Chem. 1982; 47: 757

• 197 Janosik T, Lipson AC, Gribble GW. Org. Prep. Proced. Int. 2004; 36: 289

• 198 Davis DA, Cory M, Fairley TA, Gribble GW. ARKIVOC iii, 2019; 53 available online at www.arkat-usa.org/

• 199 Wu J.-P, Sanyal S, Lu Z.-H, Senanayake CH. Tetrahedron Lett. 2009; 50: 5667

• 200 Naka H, Akagi Y, Yamada K, Imahori T, Kasahara T, Kondo Y. Eur. J. Org. Chem. 2007; 4635

• 201 Cheng L, Liu L, Sui Y, Wang D, Chen Y.-J. Tetrahedron: Asymmetry 2007; 18: 1833

• 202 Berry JM, Bradshaw TD, Fichtner I, Ren R, Schwalbe CH, Wells G, Chew E.-H, Stevens MFG, Westwell AD. J. Med. Chem. 2005; 48: 639

• 203 Vazquez E, Davies IW, Payack JF. J. Org. Chem. 2002; 67: 7551

• 204 Ishikura M, Takahashi N, Yamada K, Yanada R. Tetrahedron 2006; 62: 11 580

• 205 Denmark SE, Baird JD, Regens CS. J. Org. Chem. 2008; 73: 1440

• 206 Denmark SE, Baird JD. Org. Lett. 2004; 6: 3649

• 207 Bouissane L, Sestelo JP, Sarandeses LA. Org. Lett. 2009; 11: 1285

• 208 Pena MA, Pérez Sestelo J, Sarandeses LA. J. Org. Chem. 2007; 72: 1271

• 209 Natho P, Yang Z, Allen LAT, Rey J, White AJP, Parsons PJ. Org. Biomol. Chem. 2021; 19: 4048

• 210 Katritzky AR, Akutagawa K. Tetrahedron Lett. 1985; 26: 5935

• 211 Bergman J, Venemalm L. Tetrahedron Lett. 1988; 29: 2993

• 212 Bergman J, Venemalm L. J. Org. Chem. 1992; 57: 2495

• 213 Wincent E, Shirani H, Bergman J, Rannug U, Janosik T. Bioorg. Med. Chem. 2009; 17: 1648

• 214 Shirani H, Bergman J, Janosik T. Tetrahedron 2009; 65: 8350

• 215 Sanz R, Ignacio JM, Castroviejo MP, Fañanás FJ. ARKIVOC iv, 2007; 84 available online at www.arkat-usa.org/

• 216 Prochnow T, Maroneze A, Back DF, Zeni G. J. Org. Chem. 2019; 84: 2891

• 217 Artemova NV, Chevykalova MN, Luzikov YN, Nifant’ev IE, Nifant’ev EE. Tetrahedron 2004; 60: 10 365

• 218 Panda S, Ready JM. J. Am. Chem. Soc. 2017; 139: 6038

• 219 Panda S, Ready JM. J. Am. Chem. Soc. 2018; 140: 13 242

• 220 Silvi M, Schrof R, Noble A, Aggarwal VK. Chem.–Eur. J. 2018; 24: 4279

• 221 Das S, Daniliuc CG, Studer A. Angew. Chem. Int. Ed. 2018; 57: 4053

• 222 Das KK, Panda S. Chem.–Eur. J. 2020; 26: 14 270

• 223 Paul A, Seidel D. J. Am. Chem. Soc. 2019; 141: 8778

• 224 Saulnier MG, Gribble GW. J. Org. Chem. 1983; 48: 2690

• 225 Gribble GW, Barden TC. J. Org. Chem. 1985; 50: 5900

• 226 Amat M, Hadida S, Sathyanarayana S, Bosch J. J. Org. Chem. 1994; 59: 10

• 227 Amat M, Sathyanarayana S, Hadida S, Bosch J. Tetrahedron Lett. 1994; 35: 7123

• 228 Amat M, Sathyanarayana S, Hadida S, Bosch J. Heterocycles 1996; 43: 1713

• 229 Amat M, Seffar F, Llor N, Bosch J. Synthesis 2001; 267

• 230 Lin Q, Li J, Wang Y, Zang J. Chem. Biol. Drug Des. 2023; 101: 760

• 231 Fan A, Li SM. Adv. Synth. Catal. 2013; 355: 2659

• 232 Alexandre F.-R, Amador A, Bot S, Caillet C, Convard T, Jakubik J, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Roland A, Seifer M, Standring D, Storer R, Dousson CB. J. Med. Chem. 2011; 54: 392

• 233 Mosquera Á, Riveiros R, Sestelo JP, Sarandeses LA. Org. Lett. 2008; 10: 3745

• 234 Shirani H, Stensland B, Bergman J, Janosik T. Synlett 2006; 2459

• 235 Martin JS, Mackenzie CJ, Gilbert IH. J. Org. Chem. 2021; 86: 11 333

• 236 Garg NK, Sarpong R, Stoltz BM. J. Am. Chem. Soc. 2002; 124: 13 179

• 237 So CM, Zhou Z, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2008; 47: 6402

• 238 Yokokawa F, Sugiyama H, Aoyama T, Shioiri T. Synthesis 2004; 1476

• 239 So CM, Yuen OY, Ng SS, Chen Z. ACS Catal. 2021; 11: 7820

• 240 Ueda I, Nishiura M, Takahashi T, Eda K, Hashimoto M, Yamamura K. Tetrahedron Lett. 2006; 47: 8535

• 241 Liu Y, Gribble GW. Tetrahedron Lett. 2002; 43: 7135

• 242 Liu Y, Gribble GW. Tetrahedron Lett. 2001; 42: 2949

• 243 Liu Y, Gribble GW. Tetrahedron Lett. 2000; 41: 8717

• 244 O’Brien CJ, Nicewicz DA. Synlett 2021; 32: 814

• 245 Schlosser M, Ginanneschi A, Leroux F. Eur. J. Org. Chem. 2006; 2956

• 246 Goetz AE, Shah TK, Garg NK. Chem. Commun. (Cambridge) 2015; 51: 34

• 247 Buszek KR, Luo D, Kondrashov M, Brown N, VanderVelde D. Org. Lett. 2007; 9: 4135

• 248 Cai X, Snieckus V. Org. Lett. 2004; 6: 2293

• 249 Gribble GW, Fraser HL, Badenock JC. Chem. Commun. (Cambridge) 2001; 805

• 250 Basset J, Romero M, Serra T, Pujol MD. Tetrahedron 2012; 68: 356

• 251 Ghinato S, Dilauro G, Perna FM, Capriati V, Blangetti M, Prandi C. Chem. Commun. (Cambridge) 2019; 55: 7741

• 252 Zhao Z, Jaworski A, Piel I, Snieckus V. Org. Lett. 2008; 10: 2617

• 253 Kalepu J, Gandeepan P, Ackermann L, Pilarski LT. Chem. Sci. 2018; 9: 4203

• 254 Iwao M. Heterocycles 1993; 36: 29

• 255 Iwao M, Motoi O. Tetrahedron Lett. 1995; 36: 5929

• 256 Chauder B, Larkin A, Snieckus V. Org. Lett. 2002; 4: 815

• 257 Pérez-Serrano L, Casarrubios L, Domínguez G, Freire G, Pérez-Castells J. Tetrahedron 2002; 58: 5407

• 258 Fukuda T, Akashima H, Iwao M. Tetrahedron 2005; 61: 6886

• 259 Griffen EJ, Roe DG, Snieckus V. J. Org. Chem. 1995; 60: 1484

• 260 Mesganaw T, Fine Nathel NF, Garg NK. Org. Lett. 2012; 14: 2918

• 261 Fukuda T, Maeda R, Iwao M. Tetrahedron 1999; 55: 9151

• 262 Hartung CG, Fecher A, Chapell B, Snieckus V. Org. Lett. 2003; 5: 1899

• 263 Sharma E, Kaur M, Kaur B, Kaur A, Singh P, Singh KN. Synlett 2022; 33: 84

• 264 Im GYJ, Bronner SM, Goetz AE, Paton RS, Cheong PHY, Houk KN, Garg NK. J. Am. Chem. Soc. 2010; 132: 17 933

• 265 Murakami K, Yamada S, Kaneda T, Itami K. Chem. Rev. 2017; 117: 9302

• 266 Marsais F, Quéguiner G. Tetrahedron 1983; 39: 2009

• 267 Quéguiner G, Marsais F, Snieckus V, Epsztajn J. Adv. Heterocycl. Chem. 1991; 52: 187

• 268 Mongin F, Quéguiner G. Tetrahedron 2001; 57: 4059

• 269 Manolikakes SM, Barl NM, Sämann C, Knochel P. Z. Naturforsch., B 2013; 68: 411

• 270 Kinsman AC, Snieckus V. Tetrahedron Lett. 1999; 40: 2453

• 271 Verbeek J, Brandsma L. J. Org. Chem. 1984; 49: 3857

• 272 Ziegler K, Zeiser H. Ber. Dtsch. Chem. Ges. B 1930; 63: 1847

• 273 Giam CS, Stout JL. J. Chem. Soc. D 1969; 142

• 274 Giam CS, Knaus EE, Pasutto FM. J. Org. Chem. 1974; 39: 3565

• 275 Collum DB, McNeil AJ, Ramirez A. Angew. Chem. Int. Ed. 2007; 46: 3002

• 276 Gros P, Fort Y, Quéguiner G, Caubère P. Tetrahedron Lett. 1995; 36: 4791

• 277 Gros P, Fort Y, Caubère P. J. Chem. Soc., Perkin Trans. 1 1997; 3071

• 278 Choppin S, Gros P, Fort Y. Org. Lett. 2000; 2: 803

• 279 Choppin S, Gros P, Fort Y. Eur. J. Org. Chem. 2001; 603

• 280 Doudouh A, Woltermann C, Gros PC. J. Org. Chem. 2007; 72: 4978

• 281 Kaminski T, Gros P, Fort Y. Eur. J. Org. Chem. 2003; 3855

• 282 Mamane V, Fort Y. J. Org. Chem. 2005; 70: 8220

• 283 Cuperly D, Gros P, Fort Y. J. Org. Chem. 2002; 67: 238

• 284 Martineau D, Gros P, Fort Y. J. Org. Chem. 2004; 69: 7914

• 285 Gros PC, Doudouh A, Woltermann C. Chem. Commun. (Cambridge) 2006; 2673

• 286 Gros PC, Doudouh A, Woltermann C. Tetrahedron Lett. 2008; 49: 4717

• 287 Rodriguez AL, Gros P, Fort Y. Tetrahedron: Asymmetry 2001; 12: 2631

• 288 Khartabil HK, Gros PC, Fort Y, Ruiz-López MF. J. Am. Chem. Soc. 2010; 132: 2410

• 289 Bellan AB, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 1838

• 290 Chambers RD, Drakesmith FG, Musgrave WKR. J. Chem. Soc. 1965; 5045

• 291 Abramovitch RA, Saha M, Smith EM, Coutts RT. J. Am. Chem. Soc. 1967; 89: 1537

• 292 Gribble GW, Saulnier MG. Tetrahedron Lett. 1980; 21: 4137

• 293 Meyers AI, Gabel RA. Tetrahedron Lett. 1978; 227

• 294 Watanabe M, Snieckus V. J. Am. Chem. Soc. 1980; 102: 1457

• 295 Epsztajn J, Berski Z, Brzeziński JZ, Jóźwiak A. Tetrahedron Lett. 1980; 21: 4739

• 296 Katritzky AR, Rahimi-Rastgoo S, Ponkshe NK. Synthesis 1981; 127

• 297 Heinz B, Djukanovic D, Filipponi P, Martin B, Karaghiosoff K, Knochel P. Chem. Sci. 2021; 12: 6143

• 298 Frischmuth A, Fernández M, Barl NM, Achrainer F, Zipse H, Berionni G, Mayr H, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2014; 53: 7928

• 299 Becker MR, Ganiek MA, Knochel P. Chem. Sci. 2015; 6: 6649

• 300 Bobbio C, Schlosser M. J. Org. Chem. 2005; 70: 3039

• 301 Mamane V, Peluso P, Aubert E, Cossu S, Pale P. J. Org. Chem. 2016; 81: 4576

• 302 Wu Y.-J, Porter GJ, Frennesson DB, Saulnier MG. J. Org. Chem. 2022; 87: 2559

• 303 Miller RE, Rantanen T, Ogilvie KA, Groth U, Snieckus V. Org. Lett. 2010; 12: 2198

• 304 Mallet M, Quéguiner G. Tetrahedron 1979; 35: 1625

• 305 Miah MAJ, Snieckus V. J. Org. Chem. 1985; 50: 5436

• 306 Tsukazaki M, Snieckus V. Heterocycles 1993; 35: 689

• 307 Liu Y, Ding Q, Wu X. J. Org. Chem. 2008; 73: 6025

• 308 Daykin LM, Siddle JS, Ankers AL, Batsanov AS, Bryce MR. Tetrahedron 2010; 66: 668

• 309 Alessi M, Larkin AL, Ogilvie KA, Green LA, Lai S, Lopez S, Snieckus V. J. Org. Chem. 2007; 72: 1588

• 310 Inoue K, Hirano K, Fujioka S, Uchiyama M, Mori A, Okano K. ACS Catal. 2023; 13: 3788

• 311 Coppi DI, Salomone A, Perna FM, Capriati V. Angew. Chem. Int. Ed. 2012; 51: 7532

• 312 Rouquet G, Blakemore DC, Ley SV. Chem. Commun. (Cambridge) 2014; 50: 8908

• 313 Chartoire A, Comoy C, Fort Y. J. Org. Chem. 2010; 75: 2227

• 314 Gilman H, Spatz SM. J. Org. Chem. 1951; 16: 1485

• 315 Dagousset G, François C, León T, Blanc R, Sansiaume-Dagousset E, Knochel P. Synthesis 2014; 46: 3133

• 316 Bouillon A, Lancelot J.-C, Collot V, Bovy PR, Rault S. Tetrahedron 2002; 58: 4369

• 317 Bouillon A, Lancelot J.-C, Collot V, Bovy PR, Rault S. Tetrahedron 2002; 58: 2885

• 318 Sutherland A, Gallagher T, Sharples CGV, Wonnacott S. J. Org. Chem. 2003; 68: 2475

• 319 Liu Y, Milo LJ, Lai JH. ARKIVOC i, 2013; 135 available online at www.arkat-usa.org/

• 320 Haas D, Hammann JM, Greiner R, Knochel P. ACS Catal. 2016; 6: 1540

• 321 Dick GR, Woerly EM, Burke MD. Angew. Chem. Int. Ed. 2012; 51: 2667

• 322 Hodgson PB, Salingue FH. Tetrahedron Lett. 2004; 45: 685

• 323 Chen K, Peterson R, Math SK, LaMunyon JB, Testa CA, Cefalo DR. Tetrahedron Lett. 2012; 53: 4873

• 324 Dick GR, Knapp DM, Gillis EP, Burke MD. Org. Lett. 2010; 12: 2314

• 325 Nagaki A, Yamada S, Doi M, Tomida Y, Takabayashi N, Yoshida J.-i. Green Chem. 2011; 13: 1110

• 326 Llaveria J, Leonori D, Aggarwal VK. J. Am. Chem. Soc. 2015; 137: 10 958

• 327 Murie VE, Nishimura RHV, Rolim LA, Vessecchi R, Lopes NP, Clososki GC. J. Org. Chem. 2018; 83: 871

• 328 Blakemore PR, Kilner C, Milicevic SD. J. Org. Chem. 2005; 70: 373

• 329 Uzelac M, Mulvey RE. Chem.–Eur. J. 2018; 24: 7786

• 330 Brikci-Nigassa N, Bentabed-Ababsa G, Erb W, Mongin F. Synthesis 2018; 50: 3615

• 331 Uchiyama M, Naka H, Matsumoto Y, Ohwada T. J. Am. Chem. Soc. 2004; 126: 10 526

• 332 Uzelac M, Kennedy AR, Hevia E, Mulvey RE. Angew. Chem. Int. Ed. 2016; 55: 13 147

• 333 Ple N, Turck A, Couture K, Quéguiner G. J. Org. Chem. 1995; 60: 3781

• 334 Seggio A, Chevallier F, Vaultier M, Mongin F. J. Org. Chem. 2007; 72: 6602

• 335 Turck A, Plé N, Mojovic L, Quéguiner G. J. Heterocycl. Chem. 1990; 27: 1377

• 336 Mattson RJ, Sloan CP. J. Org. Chem. 1990; 55: 3410

• 337 Clapham KM, Batsanov AS, Greenwood RDR, Bryce MR, Smith AE, Tarbit B. J. Org. Chem. 2008; 73: 2176

• 338 Berghian C, Darabantu M, Turck A, Plé N. Tetrahedron 2005; 61: 9637

• 339 Schlosser M, Lefebvre O, Ondi L. Eur. J. Org. Chem. 2006; 1593

• 340 Busch M, Schlageter M, Weingand D, Gehring T. Chem.–Eur. J. 2009; 15: 8251

• 341 Weidmann N, Nishimura RHV, Harenberg JH, Knochel P. Synthesis 2021; 53: 557

• 342 Kenny RT, Liu F. Asian J. Org. Chem. 2022; 11 e202100787

• 343 Berghian C, Condamine E, Plé N, Turck A, Silaghi-Dumitrescu I, Maiereanu C, Darabantu M. Tetrahedron 2006; 62: 7339