Remote Steric Control for Site-Selective Synthesis

Sobi Asako; Laurean Ilies

doi:10.1055/a-2126-1835

Synlett, Table of Contents

Synlett 2023; 34(18): 2110-2116
DOI: 10.1055/a-2126-1835

new tools

Modern Boron Chemistry: 60 Years of the Matteson Reaction

Remote Steric Control for Site-Selective Synthesis

Sobi Asako ∗

,

Laurean Ilies ∗

Abstract

All articles of this category

Abstract

Control of site selectivity for organic synthesis in general, and for transition-metal-catalyzed C–H functionalization in particular, is an important and challenging task. Steric interactions have been widely used to control reaction selectivity, but these strategies are largely limited to proximity sites. Recently, control of site selectivity through remote steric interactions has emerged as an attractive strategy that can enable selective reactions at distal sites from a steric marker. This review will cover recent developments in this area, with a focus on borylation reactions and transition-metal-catalyzed C–H activation.

Key words

steric control - site selectivity - remote control - C–H activation - transition-metal catalysis

Full Text

References

References and Notes

Selected reviews:

1a Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
1b Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
1c Hartwig JF. J. Am. Chem. Soc. 2016; 138: 2

2a Lu G, Liu RY, Yang Y, Fang C, Lambrecht DS, Buchwald SL, Liu P. J. Am. Chem. Soc. 2017; 139: 16548
2b Saper NI, Ohgi A, Small DW, Semba K, Nakao Y, Hartwig JF. Nat. Chem. 2020; 12: 276
2c Singha S, Buchsteiner M, Bistoni G, Goddard R, Fürstner A. J. Am. Chem. Soc. 2021; 143: 5666

3a Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
3b Cho JY, Tse MK, Holmes D, Maleczka RE. Jr, Smith MR. III. Science 2002; 295: 305

Selected reviews:

4a Ishiyama T, Miyaura N. Pure Appl. Chem. 2006; 78: 1369
4b Mkhalid IA. I, Barnard JH, Marder TB, Murphy JB, Hartwig JF. Chem. Rev. 2010; 11: 890
4c Hartwig JF. Acc. Chem. Res. 2012; 45: 864
4d Xu L, Wang G, Zhang S, Wang H, Wang L, Liu L, Jiao J, Li P. Tetrahedron 2017; 73: 7123

5 Hall DG. Boronic Acids 2005; pp 1-676

6a Tamura H, Yamazaki H, Sato H, Sakaki S. J. Am. Chem. Soc. 2003; 125: 16114
6b Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF. J. Am. Chem. Soc. 2005; 127: 14263
6c Green AG, Liu P, Merlic CA, Houk KN. J. Am. Chem. Soc. 2014; 136: 4575

7a Vanchura BA. II, Preshlock SM, Roosen PC, Kallepalli VA, Staples RJ, Maleczka RE. Jr, Singleton DA, Smith MR. III. Chem. Commun. 2010; 46: 7724
7b Tajuddin H, Harrisson P, Bitterlich B, Collings JC, Sim N, Batsanov AS, Cheung MS, Kawamorita S, Maxwell AC, Shukla L, Morris J, Lin Z, Marder TB, Steel PG. Chem. Sci. 2012; 3: 3505
7c Green AG, Liu P, Merlic CA, Houk KN. J. Am. Chem. Soc. 2014; 136: 4575

8a Tamura H, Yamazaki H, Sato H, Sakaki S. J. Am. Chem. Soc. 2003; 125: 16114
8b Tzschucke CC, Murphy JM, Hartwig JF. Org. Lett. 2007; 9: 761
8c Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF. J. Am. Chem. Soc. 2005; 127: 14263

9a Tzschucke CC, Murphy JM, Hartwig JF. Org. Lett. 2007; 9: 757
9b Finke AD, Moore JS. Org. Lett. 2008; 10: 4851

10 Okumura S, Tang S, Saito T, Semba K, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2016; 138: 14699
11 Yang L, Semba K, Nakao Y. Angew. Chem. Int. Ed. 2017; 56: 4853
12 Bastidas JR. M, Chhabra A, Feng Y, Oleskey TJ, Smith MR. III, Maleczka RE. Jr. ACS Catal. 2022; 12: 2694
13 Haldar C, Bisht R, Chaturvedi J, Guria S, Hassan MM. M, Ram B, Chattopadhyay B. Org. Lett. 2022; 24: 8147
14 Mihai MT, Williams BD, Phipps RJ. J. Am. Chem. Soc. 2019; 141: 15477
15 Montero Bastidas JR, Oleskey TJ, Miller SL, Smith MR. III, Maleczka RE. Jr. J. Am. Chem. Soc. 2019; 141: 15483

Selected reviews:

16a Wheeler SE, Seguin TJ, Guan Y, Doney AC. Acc. Chem. Res. 2016; 49: 1061
16b Toste FD, Sigman MS, Miller SJ. Acc. Chem. Res. 2017; 50: 609
16c Neel AJ, Hilton MJ, Sigman MS, Toste FD. Nature 2017; 543: 637
16d Mihai MT, Genov GR, Phipps RJ. Chem. Soc. Rev. 2018; 47: 149
16e Kuroda Y, Nakao Y. Chem. Lett. 2019; 48: 1092
16f Kuninobu Y, Torigoe T. Org. Biomol. Chem. 2020; 18: 4126
16g Meng G, Lam NY. S, Lucas EL, Saint-Denis TG, Verma P, Chekshin N, Yu J.-Q. J. Am. Chem. Soc. 2020; 142: 10571
16h Sinha SK, Guin S, Maiti S, Biswas JP, Porey S, Maiti D. Chem. Rev. 2020; 122: 5682
16i Rej S, Das A, Chatani N. Coord. Chem. Rev. 2021; 431: 213683
16j Pandit S, Maiti S, Maiti D. Org. Chem. Front. 2021; 8: 4349
16k Fernández-Figueiras A, Ravutsov MA, Simeonov SP. ACS Omega 2022; 7: 6439
16l Hassan MM. M, Guria S, Dey S, Das J, Chattopadhyay B. Sci. Adv. 2023; 9: eadg3311

17 Tobis M, Chatani N. Science 2014; 343: 850

18a Saito Y, Segawa Y, Itami K. J. Am. Chem. Soc. 2015; 137: 5193
18b Haines BE, Saito Y, Segawa Y, Itami K, Musaev DG. ACS Catal. 2016; 6: 7536

19 Saito Y, Yamanoue K, Segawa Y, Itami K. Chem 2020; 6: 985
20 Cheng C, Hartwig JF. Science 2014; 343: 853
21 Kawazu R, Torigoe T, Kuninobu Y. Angew. Chem. Int. Ed. 2022; 61: e202202327
22 Specht ZG, Grotjahn DB, Moore CE, Rheingold AL. Organometallics 2013; 32: 6400
23 Ramadoss B, Jin Y, Asako S, Ilies L. Science 2022; 375: 658

Selected recent examples:

24a Berger F, Plutschack MB, Riegger J, Yu W, Speicher S, Ho M, Frank N, Ritter T. Nature 2019; 657: 223
24b Osi A, Mahaut D, Tumanov N, Fusaro L, Wouters J, Champagne B, Chardon A, Berionni G. Angew. Chem. Int. Ed. 2022; 61: e202112342
24c Dhankhar J, Hofer MD, Linden A, Čorić I. Angew. Chem. Int. Ed. 2022; 61: e202205470
24d Chan AP. Y, Jakoobi M, Wang C, O’Neill RT, Aydin GS. S, Halcovitch N, Boulatov R, Sergeev AG. J. Am. Chem. Soc. 2022; 144: 11564

25 Tse MH, Zhong R.-L, Kwong FY. ACS Catal. 2022; 12: 3507
26 Wu K, Doyle AG. Nat. Chem. 2017; 9: 779
27 Newman-Stonebraker SH, Smith SR, Borowski JE, Peters E, Gensch T, Johnson HC, Sigman MS, Doyle AG. Science 2021; 374: 301
28 Kim Y, Iwai T, Fujii S, Ueno K, Sawamura M. Chem. Eur. J. 2021; 27: 2289

29a Speelman AL, Tran BL, Erickson JD, Vasiliu M, Dixon DA, Bullock RM. Chem. Sci. 2021; 12: 11495
29b Carroll TG, Ryan DE, Erickson JD, Bullock RM, Tran BL. J. Am. Chem. Soc. 2022; 144: 13865

30a Liao K, Negretti S, Musaev DG, Bacsa J, Davies HM. L. Nature 2016; 533: 230
30b Liao K, Pickel TC, Boyarskikh V, Bacsa J, Musaev DG, Davies HM. L. Nature 2017; 551: 609
30c Fu J, Ren Z, Bacsa J, Musaev DG, Davies HM. L. Nature 2018; 564: 395
30d Mao J.-H, Wang Y.-B, Yang L, Xiang S.-H, Wu Q.-H, Cui Y, Lu Q, Lv J, Li S, Tan B. Nat. Chem. 2021; 13: 982
30e Lu X, Kawazu R, Song J, Yoshigoe Y, Torigoe T, Kuninobu Y. Org. Lett. 2021; 23: 4327