Organosilicon-Mediated Organic Synthesis (SiMOS): A Personal Account

Li Li; Yun-Long Wei; Li-Wen Xu

doi:10.1055/s-0039-1691496

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(01): 21-34
DOI: 10.1055/s-0039-1691496

account

Organosilicon-Mediated Organic Synthesis (SiMOS): A Personal Account

Autor*innen

Li Li

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou 311121, P. R. of China

^bCollege of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China eMail: liwenxu@hznu.edu.cn
Yun-Long Wei

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou 311121, P. R. of China
Li-Wen Xu∗

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, Hangzhou Normal University, Hangzhou 311121, P. R. of China

^bCollege of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, P. R. of China eMail: liwenxu@hznu.edu.cn

Abstract

Alle Artikel dieser Rubrik

Abstract

The organosilicon-mediated organic synthesis (SiMOS) has attracted much attention over the recent decades. However, the use of organosilicon reagents with novel catalytic strategies remains to be explored. This Account summarizes our group’s progress mainly based on the application of a wide variety of organosilicon reagents, including allylic silanes, trifluoromethyl silane, acylsilanes, chlorosilanes, hydrosilanes, trimethylsilyldiazomethane, trimethylsiloxyfuran, silanols, α-trimethylsilylmethylacetate, and trimethylsilylcyanide, in catalysis and organic reactions. These transformations were proved to be alternative procedures for the construction of structurally diverse compounds.

1 Introduction

2 The Exploration of New Reactivity of Organosilicon Reagent in Organic Synthesis

2.1 Allylic Silanes

2.2 Trifluomethylsilane (TMSCF₃)

2.3 Acylsilanes

2.4 Chlorosilanes and Hydrosilanes

2.5 Trimethylsilyldiazomethane (TMSD)

2.6 Trimethylsiloxyfuran

2.7 Silanols

2.8 Trimethylsilylcyanide (TMSCN)

3 Conclusion and Perspective

Key words

organosilicon - silanes - homogeneous catalysis - Lewis acid - silicon

Volltext

Referenzen

References

For recent reviews, see:

1a Huang HT, Li T, Wang JZ, Qin GP, Xiao TB. Chin. J. Org. Chem. 2019; 39: 1511
1b Tsurugi H, Mashima K. Acc. Chem. Res. 2019; 52: 769
1c Wang DX, Cao JF, Hang DD, Li WS, Feng SY. Prog. Chem. 2019; 31: 110
1d Muthukumaran N, Velappan K, Gour K, Prabusankar G. Coord. Chem. Rev. 2018; 377: 1
1e Hailes RL. N, Oliver AM, Gwyther J, Whittell GR, Manners I. Chem. Soc. Rev. 2016; 45: 5358

For recent reviews, see:

2a Chi H, Wang MY, Xiao YT, Wang FK, Joshy KS. Molecules 2018; 23: 2481
2b Tsunoyama H, Shibuta M, Nakaya M, Eguchi T, Nakajima A. Acc. Chem. Res. 2018; 51: 1735
2c Zhang LY, Yao WH, Gao YZ, Zhang CH, Yang H. Polymers 2017; 10: 794
2d Vlasova NN, Sorokin MS, Oborina EN. Appl. Organomet. Chem. 2017; 31: e3668
2e Wang D, Klein J, Mejia E. Chem. Asian J. 2017; 12: 1180
2f Remond E, Martin C, Martinez J, Cavelier F. Chem. Rev. 2016; 116: 11654

3a Zhao ZJ, Guo YJ, Tao J, Chang ZF, Lam JW. Y, Xu LW, Qiu HY, Tan BZ. Macromol. Rapid Commun. 2012; 33: 1074
3b Zhao ZJ, Jiang T, Guo YJ, Ding LY, He BR, Chang ZF, Lam JW. Y, Liu JZ, Chan CY. K, Lu P, Xu LW, Qiu HY, Tan BZ. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 2265
3c Li WD, Han SH, Lui YH, Chen JX. Chin. J. Org. Chem. 2017; 9: 2423
3d Yang Q, Liu L, Zhang WX, Xi ZF. Chin. J. Org. Chem. 2018; 38: 272

4a Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631
4b Indukuri K, Cornelissen L, Riant O. Synthesis 2016; 48: 4400

5 Paquette LA. Science 1982; 217: 793
6 Xu LW. Chiral Organosilicon Compounds. In Organosilicon Compounds: Theory and Experiment (Synthesis). Lee VY. Academic Press; London: 2017: 145
7 Allred AL, Rochow EG. J. Inorg. Nucl. Chem. 1958; 5: 264
8 Brook MA. Silicon in Organic, Organometallic, and Polymer Chemistry. Wiley-Interscience; New York: 1999
9 Reagents for Silicon-Mediated Organic Synthesis . Philip LF. John Wiley and Sons; New York: 2011

10a Rappoport Z, Apeloig Y. The Chemistry of Organic Silicon Compounds . John Wiley and Sons; New York: 1998
10b Yang MS, Xu LW, Qiu HY, Lai GQ, Jiang JX. Tetrahedron Lett. 2008; 49: 253
10c Xu LW, Ju YD, Li L, Qiu HY, Jiang JX, Lai GQ. Tetrahedron Lett. 2008; 49: 7037
10d Simon MO, Martinez R, Genêt JP, Darse S. Adv. Synth. Catal. 2009; 351: 153
10e Sakamoto S, Shimojima A, Miyasaka K, Ruan J, Terasaki O, Kuroda K. J. Am. Chem. Soc. 2009; 131: 9634
10f Tan G, Yang Y, Chu C, Zhu H, Roesky HW. J. Am. Chem. Soc. 2010; 132: 12231
10g Shoji Y, Higashihara T, Watanabe J, Ueda M. Marcromolecules 2010; 43: 805
10h Missaghi MN, Galloway JM, Kung HH. Organometallics 2010; 29: 3769

11a Beckmann J, Duthie A, Reeske G, Schürmann M. Organometallics 2005; 24: 3629
11b Liang JL, Barnes K, Akdag A, Worley SD, Worley D, Lee J, Broughton RM, Huang TS. Ind. Eng. Chem. Res. 2007; 46: 1861
11c Thompson DB, Brook MA. J. Am. Chem. Soc. 2008; 130: 32

Representative reviews:

12a Fleming I, Barbero A, Walter D. Chem. Rev. 1997; 97: 2063
12b Horn KA. Chem. Rev. 1995; 95: 1317
12c Prakash GK, Yudin AK. Chem. Rev. 1997; 97: 757
12d Paquette LA. Chem. Rev. 1986; 86: 73
12e Masse CE, Panek JS. Chem. Rev. 1995; 95: 1293
12f Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375

13a Sahoo B, Brandstadt KF, Lane TH, Gross RA. Org. Lett. 2005; 7: 3857
13b Naga N, Kihara Y, Miyanaga T, Furukawa H. Marcromolecules 2009; 42: 3454

Selected examples:

14a Franz AK, Woerpel KA. Acc. Chem. Res. 2000; 33: 813
14b Dilman AD, Ioffe SL. Chem. Rev. 2003; 103: 733
14c Naka H, Koseki D, Kondo Y. Adv. Synth. Catal. 2008; 350: 1901
14d Xu LW, Li L, Shi ZH. Adv. Synth. Catal. 2010; 352: 243
14e Leighton JL. Aldrichimica Acta 2010; 43: 3

Oxidation:

14f Mader MM, Norrby PO. J. Am. Chem. Soc. 2001; 123: 1970
14g Tamao K, Kakui T, Kumada M. J. Am. Chem. Soc. 1978; 100: 2268
14h Spletstoser JT, Zacuto PJ, Leighton JL. Org. Lett. 2008; 10: 5593
14i Fleming I, Henning R, Plaut H. J. Chem. Soc., Chem. Commun. 1984; 29

Cross-coupling:

14j Denmark SE, Pan W. Org. Lett. 2001; 3: 61
14k Denmark SE, Sweis RF. Acc. Chem. Res. 2002; 35: 835
14l Handy CJ, Manoso AS, McElroy WT, Seganish WM, DeShong P. Tetrahedron 2005; 61: 12201
14m Seganish WM, DeShong P. Org. Lett. 2006; 8: 3951
14n Denmark SE, Smith RC, Chang WT. T, Muhuhi JM. J. Am. Chem. Soc. 2009; 131: 3104
14o Denmark SE, Liu JH. C. Angew. Chem. Int. Ed. 2010; 49: 2978

Cycloaddition:

14p Tran K, Leighton JL. Adv. Synth. Catal. 2006; 348: 16
14q Halvorsen GT. W, Roush R. Org. Lett. 2007; 9: 2243
14r Baxter RD, Montgomery J. J. Am. Chem. Soc. 2008; 130: 9662

15a Chemler SR, Roush WR. Modern Carbonyl Chemistry. Otera J. Wiley-VCH; New York: 2000. Chap. 11, 403
15b Yamamoto Y, Asao N. Chem. Rev. 1993; 93: 2207

16 Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763

17a Li CJ, Zhang WC. J. Am. Chem. Soc. 1998; 120: 9102
17b Watahiki T, Oriyama T. Tetrahedron Lett. 2002; 43: 8959
17c Sinha P, Roy S. Organometallics 2004; 23: 67
17d Tang L, Ding L, Chang WX, Li J. Tetrahedron Lett. 2006; 47: 303

18 Gomes P, Gosmini C, Périchon J. Synthesis 2003; 1909
19 Shi SL, Xu LW, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 6638

20a Yanagisawa A, Nakamura Y, Arai T. Tetrahedron: Asymmetry 2004; 15: 1909
20b Solin N, Kjellgren JK, Szabó J. J. Am. Chem. Soc. 2004; 126: 7026
20c Kadota I, Yamamoto Y. Acc. Res. Chem. 2005; 38: 423

21a Hollis TK, Bosnich B. J. Am. Chem. Soc. 1995; 117: 4570
21b Bottoni A, Costa AL, Tommaso DD, Rossi I, Tagliavini E. J. Am. Chem. Soc. 1997; 119: 12131
21c Denmark SE, Su XP, Nishigaichi Y, Coe DM, Wong KT, Winter SB. D, Choi JY. J. Org. Chem. 1999; 64: 1958
21d Yamasaki S, Fujii K, Wada R, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2002; 124: 6536
21e Kinnaird JW. A, Ng PY, Kubota K, Wang X, Leighton J. J. Am. Chem. Soc. 2002; 124: 7920
21f Ogawa C, Sugiura M, Kobayashi S. Chem. Commun. 2003; 676
21g Wadamoto M, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 14556
21h Williams DR, Morales-Ramos AI, Williams CM. Org. Lett. 2006; 8: 4393 ; and references cited therein
21i Jagtap SB, Tsogoeva SB. Chem. Commun. 2006; 4747

22a Yang Y, Wang M, Wang D. Chem. Commun. 1997; 1654
22b Wang Z, Kisanga P, Verkade J. J. Org. Chem. 1999; 64: 6459
22c Rowlands GJ, Barnes WK. Chem. Commun. 2003; 2712
22d Evans DA, Aye Y, Wu J. Org. Lett. 2006; 8: 2071

23a Nosse B, Chhor RB, Jeong WB, Böhm C, Reiser O. Org. Lett. 2003; 5: 941
23b Pospíšil J, Kumamoto T, Markó I. Angew. Chem. Int. Ed. 2006; 45: 3357

24a Aoyama N, Hamada T, Manabe K, Kobayashi S. J. Org. Chem. 2003; 68: 7329
24b Wieland LC, Zerth HM, Mohan RS. Tetrahedron Lett. 2002; 43: 4597
24c Wadamoto M, Yamamoto H. J. Am. Chem. Soc. 2005; 127: 14556
24d Jung ME, Maderna A. Tetrahedron Lett. 2004; 45: 5301

25 Yang MS, Xu LW, Zhang FB, Qiu HY, Jiang JX, Lai GQ. Appl. Organomet. Chem. 2008; 22: 177
26 Yang MS, Xu LW, Qiu HY, Lai GQ, Jiang JX. Tetrahedron Lett. 2008; 49: 253

27a Mekhalfia A, Markó IE. Tetrahedron Lett. 1991; 32: 4779
27b Watahiki T, Akabane Y, Oriyama T. Org. Lett. 2003; 5: 3045
27c Anzalone PW, Mohan RS. Synthesis 2005; 2661

28 Du Y, Xu LW, Shimizu Y, Oisaki K, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2008; 130: 16146

29a Greene TW, Wuts PG. M. In Protective Groups in Organic Synthesis, 3rd ed. Wiley-Interscience; New York: 1999. Chap. 2
29b Stolarzewicz A, Grobelny Z, Pisarski W, Losiewicz B, Peikarnik B, Swinarew A. Eur. J. Org. Chem. 2006; 2485
29c Corma A, Renz M. Angew. Chem. Int. Ed. 2007; 46: 298

30a Colvin E. Silicon in Organic Synthesis. Butterworth; London: 1981: 97
30b Weber WP. Silicon Reagents for Organic Synthesis. Vol. 12. Springer; Berlin: 1983: 173
30c Majetich G, Behnke M, Hull K. J. Org. Chem. 1985; 50: 3615
30d Hosomi A. Acc. Chem. Res. 1988; 21: 200
30e Fleming I, Dunogues J, Smithers R. Org. React. 1989; 37: 57
30f Langkopf E, Schinzer D. Chem. Rev. 1995; 95: 1375
30g Tori M, Makino C, Hisazumi K, Sono M, Nakashima K. Tetrahedron: Asymmetry 2001; 12: 301

31a Schinzer D. Angew. Chem., Int. Ed. Engl. 1984; 23: 308
31b Kuhnert N, Peverley J, Robertson J. Tetrahedron Lett. 1998; 39: 3215
31c Lee PH, Lee K, Sung SY, Chang S. J. Org. Chem. 2001; 66: 8646
31d Yadav JS, Reddy BV. S, Sadasiv K, Satheesh G. Tetrahedron Lett. 2002; 43: 9695
31e Lee PH, Seomoon D, Kim S, Nagaiah K, Damle SV, Lee K. Synthesis 2003; 2189
31f Stevens BD, Nelson SG. J. Org. Chem. 2005; 70: 4375

32a Zhou W, Li L, Xu LW, Qiu HY, Lai GQ, Xia CG. Synth. Commun. 2008; 38: 1638
32b Gao YH, Yang L, Zhou W, Xu LW, Xia CG. Appl. Organomet. Chem. 2009; 23: 114
32c Jiang ZY, Wu JR, Li L, Chen XH, Lai GQ, Jiang JX. Cent. Eur. J. Chem. 2010; 8: 669
32d Jiang ZY, Zhang CH, Gu FL, Yang KF, Lai GQ, Xu LW. Synlett 2010; 1251
32e Yang HM, Gao YH, Li L, Jiang ZY, Lai GQ, Xia CG, Xu LW. Tetrahedron Lett. 2010; 51: 3836

33 Xu LW, Yang MS, Qiu HY, Lai GQ, Jiang JX. Synth. Commun. 2008; 38: 1011

34a Nie J, Guo HC, Cahard D, Ma JA. Chem. Rev. 2011; 111: 455
34b Dolfen J, de Kimpe N, Dhooghe M. Synlett 2016; 27: 1486
34c Ma JA, Cahard D. Chem. Rev. 2004; 104: 6119
34d Caron S, Do NM, Sieser JE, Arpin P, Vazquez E. Org. Process Res. Dev. 2007; 11: 1015
34e Boechat N, Bastos MM. Curr. Org. Chem. 2010; 7: 403

35a Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
35b Zhang C. Adv. Synth. Catal. 2017; 365: 372

36 Dong C, Bai XF, Lv JY, Cui YM, Cao J, Zheng ZJ, Xu LW. Molecules 2017; 22: 769

Reviews:

37a Ricci A, Degl’Innocenti A. Synthesis 1986; 647
37b Jurczak J, Golebiowski A. Chem. Rev. 1989; 89: 149
37c Page PC. B, Klair SS, Rosenthal S. Chem. Soc. Rev. 1990; 19: 147

For our work on copper-catalyzed conjugate addition of diethylzinc to α,β-unsaturated acylsilanes, see:

37d Ye F, Zheng ZJ, Deng WH, Zheng LS, Deng Y, Xia CG, Xu LW. Chem. Asian J. 2013; 8: 2242
37e Lv JY, Zheng ZJ, Li L, Cui YM, Xu Z, Cao J, Yang KF, Xu LW. RSC Adv. 2017; 7: 54934

38a Corey EJ, Luo G, Lin LS. Angew. Chem. Int. Ed. 1998; 37: 1126
38b Berber H, Brigaud T, Lefebvre O, Plantier-Royon R, Portella C. Chem. Eur. J. 2001; 7: 903
38c Nicewicz DA, Satterfirld AD, Schmit DC, Johnson JS. J. Am. Chem. Soc. 2008; 130: 17281
38d Behenna DC, Corey EJ. J. Am. Chem. Soc. 2008; 130: 6720
38e Lettan RB. II, Woodward CC, Scheidt KA. Angew. Chem. Int. Ed. 2008; 47: 2294

39 Zhang HJ, Pribbenow DL, Bolm C. Chem. Soc. Rev 2013; 42: 8540

40a Paredes MD, Alonso R. J. Org. Chem. 2000; 65: 2292
40b Nicewicz DA, Yates CM, Johnson JS. J. Org. Chem. 2004; 69: 6548

41 Honda M, Ohkura N, Saisyo S.-I, Segi M, Nakajima T. Tetrahedron 2003; 59: 8203
42 Bai XF, Gao G, Zheng ZJ, Li F, Lai GQ, Jiang K, Li F, Xu LW. Synlett 2011; 3031

43a Takeda K, Ohnishi Y, Koizumi T. Org. Lett. 1999; 1: 237
43b Arai N, Suzuki K, Sugizaki S, Sorimachi H, Ohkuma T. Angew. Chem. Int. Ed. 2008; 47: 1770

44 Gao G, Bai XF, Li F, Zheng LS, Zheng ZJ, Lai GQ, Jiang K, Li F, Xu LW. Tetrahedron Lett. 2012; 53: 2164

45a Shen H, Lu X, Jiang KZ, Yang KF, Lu Y, Zheng ZJ, Lai GQ, Xu LW. Tetrahedron Lett. 2012; 68: 8916
45b Bai XF, Deng WH, Xu Z, Li FW, Deng Y, Xia CG, Xu LW. Chem. Asian J. 2014; 9: 1108

46 Xu LW, Li L, Xia CG, Zhao PQ. Tetrahedron Lett. 2004; 45: 2435

47a Xu LW, Wang ZT, Xia CG, Li L, Zhao PQ. Helv. Chim. Acta. 2004; 87: 2608
47b Xu LW, Xia CG. Synthesis 2004; 2191
47c Xu LW, Xia CG. Tetrahedron Lett. 2004; 45: 4507
47d Xu LW, Xia CG, Li L. J. Org. Chem. 2004; 69: 8482
47e Xu LW, Xia CG, Hu XX. Chem. Commun. 2003; 2570
47f Yang L, Xu LW, Xia CG. Tetrahedron Lett. 2007; 48: 1599
47g Xu LW, Zhou W, Yang L, Xia CG. Synth. Commun. 2007; 38: 3095
47h Deng WH, Ye F, Bai XF, Li L, Song T, Wei YL, Xu LW. RSC Adv. 2014; 4: 479

48a Yang HM, Li L, Li F, Jiang KZ, Shang JY, Lai GQ, Xu LW. Org. Lett. 2011; 13: 6508
48b Cai YF, Li L, Luo MX, Yang KF, Lai GQ, Jiang JX, Xu LW. Chirality 2011; 23: 397

49 Xu LW, Chen XH, Shen H, Deng Y, Jiang JX, Jiang K, Lai GQ, Sheng CQ. Eur. J. Org. Chem. 2012; 290

50a Peterson DJ. J. Org. Chem. 1968; 33: 780
50b Ager DJ. Org. React. 1990; 38: 1
50c Assadi N, Pogodin S, Agranat I. Eur. J. Org. Chem. 2011; 6773
50d Wei GQ, Cohen T. Synlett 2011; 2697
50e McNulty J, Das P, Gosciniak D. Tetrahedron Lett. 2008; 49: 281
50f Fernandez MC, Diaz A, Guillin JJ, Blanco O, Ruiz M, Ojea V. J. Org. Chem. 2006; 71: 6958
50g Pulido FJ, Barberdo A. Nat. Protoc. 2006; 1: 2068

51a Robert P, Roman R. J. Organomet. Chem. 1988; 341: 549
51b Yu J, Spencer JB. J. Am. Chem. Soc. 1997; 119: 5257
51c Yu J, Gaunt M, Spencer JB. J. Org. Chem. 2002; 67: 4627
51d Dunne JO, Duckett SB, Konya D, Leñero KQ, Drent E. J. Am. Chem. Soc. 2004; 126: 16708
51e Kluwer AM, Koblenz TS, Jonischkeit T, Woelk K, Elesevier C. J. Am. Chem. Soc. 2005; 127: 15470
51f Kim IS, Dong GR, Jung YH. J. Org. Chem. 2007; 72: 5424
51g Brandt B, Fischer J.-H, Ludwig W, Libuda J, Zaera F, Schauermann S, Freund H.-J. J. Phys. Chem. C 2008; 112: 11408

52 Bai XF, Xu LW, Zheng LS, Jiang JX, Lai GQ, Shang JY. Chem. Eur. J. 2012; 18: 8174

53a Wang H, Li L, Bai XF, Shang JY, Yang KF, Xu LW. Adv. Synth. Catal. 2013; 355: 341
53b Wang H, Li L, Bai XF, Deng WH, Zheng ZJ, Yang KF, Xu LW. Green Chem. 2013; 15: 2349
53c Wang H, Yang KF, Li L, Bai Y, Zheng ZJ, Zhang WQ, Gao Z, Xu LW. ChemCatChem 2014; 6: 580
53d Wang H, Zhang J, Cui YM, Yang KF, Zheng ZJ, Xu LW. RSC Adv. 2014; 4: 34681
53e Dong XY, Lin Y, Cui YM, Yang KF, Zheng ZJ, Xu LW. ChemistrySelect 2016; 1: 2400
53f Li N, Dong XY, Zhang JL, Yang KF, Gao ZW, Zheng ZJ, Zhang WQ, Xu LW. RSC Adv. 2017; 7: 50729
53g Long PW, Xu JX, Bai XF, Xu Z, Zheng ZJ, Yang KF, Li L, Xu LW. RSC Adv. 2018; 8: 22944

54 Schramm Y, Barrios-Landeros F, Pfaltz A. Chem. Sci. 2013; 4: 2760
55 Wang H, Yang KF, Li L, Bai Y, Zheng ZJ, Zhang WQ, Gao ZW, Xu LW. ChemCatChem 2014; 6: 580
56 Bai XF, Song T, Deng WH, Wei YL, Li L, Xia CG, Xu LW. Synlett 2014; 25: 417

57a Corey JY, Braddock-Wilking J. Chem. Rev. 1999; 99: 175
57b Shang JY, Li F, Bai XF, Jiang JX, Yang KF, Lai GQ, Xu LW. Eur. J. Org. Chem. 2012; 2809

58 Chen XH, Xu LW, Deng Y, Jiang KZ, Lai GQ, Ni Y, Yang KF, Jiang JX. Eur. J. Org. Chem. 2011; 1736

For recent reviews, see:

59a Xia Y, Qiu D, Wang J. Chem. Rev. 2017; 117: 13810
59b Xia Y, Wang J. Chem. Soc. Rev. 2017; 46: 2306

60 Mu QC, Wang XB, Ye F, Sun YL, Bai XF, Chen J, Xia CG, Xu LW. Chem. Commun. 2018; 54: 12994
61 Themed issue on Recent Advances in Organosilicon Chemistry directed towards Organic Synthesis: Langer, P. Ed.; Tetrahedron 2009, 65, 5445.

62a Wieland LC, Vieira EM, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2009; 131: 570
62b Mandai H, Mandai K, Snapper ML, Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 17961

63 Casiraghi G, Battistini L, Curti C, Rassu G, Zanardi F. Chem. Rev. 2011; 111: 3076

64a Xu Z, Xu LW. Chem. Rec. 2015; 15: 925
64b Zheng LS, Li L, Yang KF, Zheng ZJ, Xiao XQ, Xu LW. Tetrahedron 2013; 69: 8777

65 Krenske EH, Houk KN. Acc. Chem. Res. 2013; 46: 979
66 Habata Y, Taniguchi A, Ikeda M, Hiraoka T, Matsuyama N, Otsuka S, Kuwahara S. Inorg. Chem. 2013; 52: 2542

For recent examples, see:

67a Wang K, Zhou J, Jiang Y, Zhang M, Wang C, Xue D, Tang W, Sun H, Xiao J, Li C. Angew. Chem. Int. Ed. 2019; 58: 6380
67b Roesch P, Meller R, Dallmann A, Scholz G, Kaupp M, Braun T, Braun-Cula B, Wittwer P. Chem. Eur. J. 2019; 25: 4678
67c Koo J, Kim SH, Hong SH. Chem. Commun. 2018; 54: 4995

68 Ye F, Zheng ZJ, Li L, Yang KF, Xia CG, Xu LW. Chem. Eur. J. 2013; 19: 15452

69a Gavrilov KN, Zheglov SV, Rastorguev EA, Groshkin NN, Maksimova MG, Benetsky EB, Davankov VA, Reetz MT. Adv. Synth. Catal. 2010; 352: 2599
69b Wu KH, Zhou S, Chen CA, Yang MC, Chiang RT, Chen CR, Gau HM. Chem. Commun. 2011; 47: 11668
69c Wu KH, Gau HM. J. Am. Chem. Soc. 2006; 128: 14808
69d Salvi L, Kim JG, Walsh PJ. J. Am. Chem. Soc. 2009; 131: 12483

70 Li F, Zhou W, Zheng LS, Li L, Zheng ZJ, Xu LW. Synth. Commun. 2014; 44: 2861

71a Li F, Zheng ZJ, Shang JY, Jiang KZ, Lai GQ, Jiang JX, Xu LW. Chem. Asian J. 2012; 7: 2008
71b Wei YL, Yang KF, Li F, Zheng ZJ, Xu Z, Xu LW. RSC Adv. 2014; 4: 37859

For recent reviews, see:

72a North M, Usanov DL, Young C. Chem. Rev. 2009; 108: 5146
72b Khan NH, Kureshy RI, Abdi SH. R, Agrawal S, Jasra RV. Coord. Chem. Rev. 2008; 252: 593

For selected and recent examples, see:

73a Zhang HD, Zou Y, Wang YM, Shen Y, Zheng XX. Chem. Eur. J. 2014; 20: 7830
73b Liu W, Groves JT. Angew. Chem. Int. Ed. 2013; 52: 6024

74 Wei YL, Huang WS, Cui YM, Yang KF, Xu Z, Xu LW. RSC Adv. 2015; 5: 3098

75a Xu LW, Li L, Shi ZH. Adv. Synth. Catal. 2010; 352: 243
75b Shen H, Yang KF, Shi ZH, Jiang JX, Lai GQ, Xu LW. Eur. J. Org. Chem. 2011; 5031
75c Shi ZH, Sheng H, Yang KF, Jiang JX, Lai GQ, Lu Y, Xu LW. Eur. J. Org. Chem. 2011; 66
75d Song T, Li L, Zhou W, Zheng ZJ, Deng Y, Xu Z, Xu LW. Chem. Eur. J. 2015; 21: 554
75e Chen MY, Song T, Zheng ZJ, Xu Z, Cui YM, Xu LW. RSC Adv. 2016; 6: 58698
75f Chen MY, Chen L, Xu Z, Song T, Zheng ZJ, Cao J, Cui YM, Xu LW. ChemCatChem 2018; 10: 280
75g Yuan Y, Zheng ZJ, Li L, Bai XF, Xu Z, Cui YM, Cao J, Yang KF, Xu LW. Adv. Synth. Catal. 2018; 360: 3002
75h Sun FN, Yang WC, Chen XB, Sun YL, Cao J, Xu Z, Xu LW. Chem. Sci. 2019; 10: 7579