35.2.5.1.9 Synthesis by Addition across C=C Bonds (Update 2015)

Abstract

This chapter is an update to the earlier Science of Synthesis Section 35.2.5.1, written by Troll in 2006, on the synthesis of 1-bromo-n-heteroatom-functionalized alkanes (n ≥2), with both functions formed simultaneously by addition across C=C bonds. It focuses on recent advances in the field of bromofunctionalization of alkenes in the period 2007–2014, in particular on catalytic enantioselective syntheses.

Key words

bromine compounds - carbon—bromine bonds - carbon—heteroatom bonds - bromination of alkenes - alkoxybromination of alkenes - bromolactonization - aminobromination - catalytic enantioselective reactions

• 1 Braddock DC, Cansell G, Hermitage SA. Chem. Commun. (Cambridge) 2006; 2483

• 2 Ahmad SM, Braddock DC, Cansell G, Hermitage SA. Tetrahedron Lett. 2007; 48: 915

• 3 Ahmad SM, Braddock DC, Cansell G, Hermitage SA, Redmond JM, White AJP. Tetrahedron Lett. 2007; 48: 5948

• 4 Denmark SE, Burk MT. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: 20 655

• 5 Chen F, Jiang X, Er JC, Yeung Y.-Y. Tetrahedron Lett. 2010; 51: 3433

• 6 Sawamura Y, Nakatsuji H, Sakakura A, Ishihara K. Chem. Sci. 2013; 4: 4181

• 7 Davies SG, Polywka MEC, Thomas SE. Tetrahedron Lett. 1985; 26: 1461

• 8 Davies SG, Polywka MEC, Thomas SE. J. Chem. Soc., Perkin Trans. 1 1986; 1277

• 9 Bravo F, McDonald FE, Neiwert WA, Hardcastle KI. Org. Lett. 2004; 6: 4487

• 10 Tanuwidjaja J, Ng S.-S, Jamison TF. J. Am. Chem. Soc. 2009; 131: 12 084

• 11 Bonney KJ, Braddock DC, White AJP, Yaqoob M. J. Org. Chem. 2011; 76: 97

• 12 Braddock DC. Org. Lett. 2006; 8: 6055

• 13 Braddock DC, Millan DS, Pérez-Fuertes Y, Pouwer RH, Sheppard RN, Solanki S, White AJP. J. Org. Chem. 2009; 74: 1835

• 14 Snyder SA, Treitler DS, Brucks AP, Sattler W. J. Am. Chem. Soc. 2011; 133: 15 898

• 15 Snyder SA, Brucks AP, Treitler DS, Moga I. J. Am. Chem. Soc. 2012; 134: 17 714

• 16 Zhou L, Tan CK, Zhou J, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 10 245

• 17 Chen J, Chng S, Zhou L, Yeung Y.-Y. Org. Lett. 2011; 13: 6456

• 18 Ke Z, Yeung Y.-Y. Org. Lett. 2013; 15: 1906

• 19 Fujioka H, Kotoku N, Sawama Y, Nagatomi Y, Kita Y. Tetrahedron Lett. 2002; 43: 4825

• 20 Fujioka H. Synlett 2012; 23: 825

• 21 Fujioka H, Nakahara K, Oki T, Hirano K, Hayashi T, Kita Y. Tetrahedron Lett. 2010; 51: 1945

• 22 Yeung Y.-Y, Hong S, Corey EJ. J. Am. Chem. Soc. 2006; 128: 6310

• 23 Yeung Y.-Y, Gao X, Corey EJ. J. Am. Chem. Soc. 2006; 128: 9644

• 24 Hajra S, Sinha D, Bhowmick M. J. Org. Chem. 2007; 72: 1852

• 25 Wang Z, Zhang Y, Fu H, Jiang Y, Zhao Y. Synlett 2008; 2667

• 26 Yadav JS, Subba Reddy BV, Narasimha Chary D, Chandrakanth D. Tetrahedron Lett. 2009; 50: 1136

• 27 Shaikh TM, Karabal PU, Suryavanshi G, Sudalai A. Tetrahedron Lett. 2009; 50: 2815

• 28 Zhang G, An G, Zheng J, Pan Y, Li G. Tetrahedron Lett. 2010; 51: 987

• 29 Silva López C, Pérez-Balado C, Rodríguez-Graña P, de Lera ÁR. Org. Lett. 2008; 10: 77

• 30 Sun Y, Li R, Zhang W, Li A. Angew. Chem. Int. Ed. 2013; 52: 9201

• 31 Chen Z.-G, Wei J.-F, Li R.-T, Shi X.-Y, Zhao P.-F. J. Org. Chem. 2009; 74: 1371

• 32 Wei J.-F, Chen Z.-G, Lei W, Zhang L.-H, Wang M.-Z, Shi X.-Y, Li R.-T. Org. Lett. 2009; 11: 4216

• 33 Zhi S, An G, Sun H, Han J, Li G, Pan Y. Tetrahedron Lett. 2010; 51: 2745

• 34 Chen Z.-G, Wang Y, Wei J.-F, Zhao P.-F, Shi X.-Y. J. Org. Chem. 2010; 75: 2085

• 35 Ji X, Duan Z, Qian Y, Han J, Li G, Pan Y. RSC Adv. 2012; 2: 5565

• 36 Sun H, Han J, Kattamuri PV, Pan Y, Li G. J. Org. Chem. 2013; 78: 1171

• 37 Zhou J, Yeung Y.-Y. Org. Lett. 2014; 16: 2134

• 38 Hajra S, Bhowmick M, Sinha D. J. Org. Chem. 2006; 71: 9237

• 39 Fridland SV, Shchukareva TM, Salakhutdinov RA. Zh. Obshch. Khim. 1976; 46: 1232

• 40 Zefirov NS, Zyk NV, Borisenko AA, Krysin MY, Schestakova TG. Tetrahedron 1983; 39: 3145

• 41 Slebocka-Tilk H, Ball RG, Brown RS. J. Am. Chem. Soc. 1985; 107: 4504

• 42 Bennet AJ, Brown RS, McClung RED, Klobukowski M, Aarts GHM, Santarsiero BD, Bellucci G, Bianchini R. J. Am. Chem. Soc. 1991; 113: 8532

• 43 Neverov AA, Brown RS. J. Org. Chem. 1996; 61: 962

• 44 Brown RS. Acc. Chem. Res. 1997; 30: 131

• 45 Rodebaugh R, Fraser-Reid B. Tetrahedron 1996; 52: 7663

• 46 Braddock DC, Hermitage SA, Kwok L, Pouwer R, Redmond JM, White AJP. Chem. Commun. (Cambridge) 2009; 1082

• 47 Denmark SE, Burk MT, Hoover AJ. J. Am. Chem. Soc. 2010; 132: 1232

• 48 Castellanos A, Fletcher SP. Chem.–Eur. J. 2011; 17: 5766

• 49 Snyder SA, Treitler DS, Brucks AP. Aldrichimica Acta 2011; 44: 27

• 50 Tan CK, Ling Z, Yeung Y.-Y. Synlett 2011; 1335

• 51 Hennecke U. Chem.–Asian J. 2012; 7: 456

• 52 Denmark SE, Kuester WE, Burk MT. Angew. Chem. Int. Ed. 2012; 51: 10 938

• 53 Chemler SR, Bovino MT. ACS Catal. 2013; 3: 1076

• 54 Tan CK, Yeung Y.-Y. Chem. Commun. (Cambridge) 2013; 49: 7985

• 55 El-Qisairi AK, Qaseer HA, Katsigras G, Lorenzi P, Trivedi U, Tracz S, Hartman A, Miller JA, Henry PM. Org. Lett. 2003; 5: 439

• 56 Whitehead DC, Fhaner M, Borhan B. Tetrahedron Lett. 2011; 52: 2288

• 57 Zhou L, Tan CK, Jiang X, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2010; 132: 15 474

• 58 Tan CK, Zhou L, Yeung Y.-Y. Org. Lett. 2011; 13: 2738

• 59 Chen J, Zhou L, Tan CK, Yeung Y.-Y. J. Org. Chem. 2012; 77: 999

• 60 Tan CK, Le C, Yeung Y.-Y. Chem. Commun. (Cambridge) 2012; 48: 5793

• 61 Jiang X, Tan CK, Zhou L, Yeung Y.-Y. Angew. Chem. Int. Ed. 2012; 51: 7771

• 62 Tay DW, Leung GYC, Yeung Y.-Y. Angew. Chem. Int. Ed. 2014; 53: 5161

• 63 Zhao Y, Jiang X, Yeung Y.-Y. Angew. Chem. Int. Ed. 2013; 52: 8597

• 64 Ke Z, Tan CK, Chen F, Yeung Y.-Y. J. Am. Chem. Soc. 2014; 136: 5627

• 65 Murai K, Matsushita T, Nakamura A, Fukushima S, Shimura M, Fujioka H. Angew. Chem. Int. Ed. 2010; 49: 9174

• 66 Murai K, Nakamura A, Matsushita T, Shimura M, Fujioka H. Chem.–Eur. J. 2012; 18: 8448

• 67 Murai K, Matsushita T, Nakamura A, Hyogo N, Nakajima J, Fujioka H. Org. Lett. 2013; 15: 2526

• 68 Ikeuchi K, Ido S, Yoshimura S, Asakawa T, Inai M, Hamashima Y, Kan T. Org. Lett. 2012; 14: 6016

• 69 Armstrong A, Braddock DC, Jones AX, Clark S. Tetrahedron Lett. 2013; 54: 7004

• 70 Zhang W, Liu N, Schienebeck CM, Zhou X, Izhar II, Guzei IA, Tang W. Chem. Sci. 2013; 4: 2652

• 71 Hennecke U, Müller CH, Fröhlich R. Org. Lett. 2011; 13: 860

• 72 Huang D, Wang H, Xue F, Guan H, Li L, Peng X, Shi Y. Org. Lett. 2011; 13: 6350

• 73 Denmark SE, Burk MT. Org. Lett. 2012; 14: 256

• 74 Li G.-x, Fu Q.-q, Zhang X.-m, Jiang J, Tang Z. Tetrahedron: Asymmetry 2012; 23: 245

• 75 Wang Y.-M, Wu J, Hoong C, Rauniyar V, Toste FD. J. Am. Chem. Soc. 2012; 134: 12 928

• 76 Liu H, Jiang G, Pan X, Wan X, Lai Y, Ma D, Xie W. Org. Lett. 2014; 16: 1908

• 77 Paull DH, Fang C, Donald JR, Pansick AD, Martin SF. J. Am. Chem. Soc. 2012; 134: 11 128

• 78 Lee HJ, Kim DY. Tetrahedron Lett. 2012; 53: 6984

• 79 Zhang Y, Xing H, Xie W, Wan X, Lai Y, Ma D. Adv. Synth. Catal. 2013; 355: 68

• 80 Zhou L, Chen J, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2011; 133: 9164

• 81 Chen J, Zhou L, Yeung Y.-Y. Org. Biomol. Chem. 2012; 10: 3808

• 82 Zhou L, Tay DW, Chen J, Leung GYC, Yeung Y.-Y. Chem. Commun. (Cambridge) 2013; 49: 4412

• 83 Alix A, Lalli C, Retailleau P, Masson G. J. Am. Chem. Soc. 2012; 134: 10 389

• 84 Chen F, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc. 2013; 135: 1232

• 85 Cai Y, Liu X, Hui Y, Jiang J, Wang W, Chen W, Lin L, Feng X. Angew. Chem. Int. Ed. 2010; 49: 6160

• 86 Cai Y, Liu X, Zhou P, Kuang Y, Lin L, Feng X. Chem. Commun. (Cambridge) 2013; 49: 8054

• 87 Huang D, Liu X, Li L, Cai Y, Liu W, Shi Y. J. Am. Chem. Soc. 2013; 135: 8101

• 88 Bovino MT, Chemler SR. Angew. Chem. Int. Ed. 2012; 51: 3923