hydrogen; palladium on activated charcoal in methanol P=760 Torr; 0.25 h;

1: DCC 2: DDQ / toluene / Heating 3: 1.) Hg(OTFA)2, 2.) KI, 3.) I2 4: Pd2(dba)3, P(o-tolyl)3, K2CO3 / toluene / Heating 5: Zn, AcOH 6: DCC 7: 93 percent / Zn, AcOH / ethyl acetate 8: 82 percent / Et3N, DMAP 9: 91 percent / Bu3P / benzene / 60 °C 10: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 11: NaBH4, AcOH 12: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: 82 percent / Et3N, DMAP 2: 91 percent / Bu3P / benzene / 60 °C 3: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 4: NaBH4, AcOH 5: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: 88 percent / DCC, DMAP 2: 81 percent / BH3*THF, TFA 3: DCC 4: DDQ / toluene / Heating 5: 1.) Hg(OTFA)2, 2.) KI, 3.) I2 6: Pd2(dba)3, P(o-tolyl)3, K2CO3 / toluene / Heating 7: Zn, AcOH 8: DCC 9: 93 percent / Zn, AcOH / ethyl acetate 10: 82 percent / Et3N, DMAP 11: 91 percent / Bu3P / benzene / 60 °C 12: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 13: NaBH4, AcOH 14: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: DCC 2: DDQ / toluene / Heating 3: 1.) Hg(OTFA)2, 2.) KI, 3.) I2 4: Pd2(dba)3, P(o-tolyl)3, K2CO3 / toluene / Heating 5: Zn, AcOH 6: DCC 7: 93 percent / Zn, AcOH / ethyl acetate 8: 82 percent / Et3N, DMAP 9: 91 percent / Bu3P / benzene / 60 °C 10: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 11: NaBH4, AcOH 12: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: 81 percent / BH3*THF, TFA 2: DCC 3: DDQ / toluene / Heating 4: 1.) Hg(OTFA)2, 2.) KI, 3.) I2 5: Pd2(dba)3, P(o-tolyl)3, K2CO3 / toluene / Heating 6: Zn, AcOH 7: DCC 8: 93 percent / Zn, AcOH / ethyl acetate 9: 82 percent / Et3N, DMAP 10: 91 percent / Bu3P / benzene / 60 °C 11: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 12: NaBH4, AcOH 13: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: 82 percent / Et3N, DMAP 2: 91 percent / Bu3P / benzene / 60 °C 3: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 4: NaBH4, AcOH 5: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: 1.) Hg(OTFA)2, 2.) KI, 3.) I2 2: Pd2(dba)3, P(o-tolyl)3, K2CO3 / toluene / Heating 3: Zn, AcOH 4: DCC 5: 93 percent / Zn, AcOH / ethyl acetate 6: 82 percent / Et3N, DMAP 7: 91 percent / Bu3P / benzene / 60 °C 8: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 9: NaBH4, AcOH 10: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 2: NaBH4, AcOH 3: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme

1: DDQ / toluene / Heating 2: 1.) Hg(OTFA)2, 2.) KI, 3.) I2 3: Pd2(dba)3, P(o-tolyl)3, K2CO3 / toluene / Heating 4: Zn, AcOH 5: DCC 6: 93 percent / Zn, AcOH / ethyl acetate 7: 82 percent / Et3N, DMAP 8: 91 percent / Bu3P / benzene / 60 °C 9: 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide / 48 h 10: NaBH4, AcOH 11: 87 percent / H2 / Pd/C / methanol / 0.25 h / 760 Torr View Scheme