2-苯基-1,2,3,4-四氢异喹啉可作为有机合成中间体和医药中间体，主要用于实验室研发过程和化工生产过程中。
医药;化工
路线1：钯催化芳基化法
- 步骤：向2-mL Biotage微波瓶中加入Pd(OAc)₂（5.6mg，5mol%）、CyJohnPhos（9.6mg，5.5mol%）、KOt-Bu（78.4mg，1.4当量）和芳基碘（0.5mmol，1当量）（固体先加）；密封后氩气吹扫，加入叔丁醇（1.0mL）、液体芳基碘（0.5mmol，1当量）和1,2,3,4-四氢异喹啉（75mL，1.2当量）；100℃微波照射5分钟，冷却后用EtOAc稀释，硅藻土过滤，滤液经饱和NaCl洗涤、MgSO₄干燥、减压浓缩得粗产物。
- 条件：以叔丁醇为溶剂，Pd(OAc)₂/CyJohnPhos为催化剂，KOt-Bu为碱，100℃微波反应5分钟，惰性气氛。
- 收率：94%
- 参考文献：[1] Chemical Communications, 2017, vol.53, #93, p.12536-12539；[2] Australian Journal of Chemistry, 2015, vol.68, #12, p.1890-1893；[3] Advanced Synthesis and Catalysis, 2017, vol.359, #16, p.2832-2846；[4] Journal of Molecular Catalysis A: Chemical, 2017, vol.426, p.398-406；[5] Monatshefte fur Chemie, 2017, vol.148, #1, p.91-104；[6] Organic and Biomolecular Chemistry, 2018, vol.16, #11, p.1971-1975；[7] Journal of Organic Chemistry, 2018, vol.83, #2, p.1000-1010；[8] Tetrahedron Letters, 2016, vol.57, #40, p.4480-4483；[9] Green Chemistry, 2018, vol.20, #18, p.4217-4223；[10] Journal of the American Chemical Society, 2018；[11] Advanced Synthesis and Catalysis, 2015, vol.357, #16-17, p.3424-3428；[12] Chemical Communications, 2011, vol.47, #42, p.11787-11789；[13] Organic and Biomolecular Chemistry, 2012, vol.10, #4, p.835-842；[14] Tetrahedron Letters, 2012, vol.53, #12, p.1456-1459；[15] Journal of Organic Chemistry, 2018, vol.83, #12, p.6754-6761；[16] Synlett, 2018, vol.29, #20, p.2697-2700；[17] Organic Letters, 2018, vol.20, #24, p.7933-7936；[18] Organic Letters, 2014, vol.16, #9, p.2346-2349；[19] European Journal of Organic Chemistry, 2017, vol.2017, #42, p.6338-6348；[20] Journal of the American Chemical Society, 2005, vol.127, #19, p.6968-6969；[21] Tetrahedron Asymmetry, 2006, vol.17, #4, p.590-597；[22] Tetrahedron Letters, 2009, vol.50, #11, p.1199-1202；[23] Organic Letters, 2008, vol.10, #17, p.3661-3663；[24] Journal of Organic Chemistry, 2009, vol.74, #19, p.7464-7469；[25] Organic and Biomolecular Chemistry, 2010, vol.8, #18, p.4077-4079；[26] Organic Letters, 2011, vol.13, #15, p.3852-3855；[27] Organic Letters, 2013, vol.15, #3, p.574-577；[28] Chemistry - A European Journal, 2013, vol.19, #20, p.6443-6450；[29] Organic Letters, 2014, vol.16, #7, p.1988-1991；[30] Organic and Biomolecular Chemistry, 2015, vol.13, #2, p.447-451；[31] Organic and Biomolecular Chemistry, 2015, vol.13, #14, p.4260-4265；[32] Organic Letters, 2015, vol.17, #16, p.3982-3985；[33] Chemical Communications, 2015, vol.51, #56, p.11256-11259；[34] Green Chemistry, 2016, vol.18, #3, p.826-833；[35] Advanced Synthesis and Catalysis, 2014, vol.356, #13, p.2846-2852；[36] Tetrahedron Letters, 2015, vol.56, #48, p.6696-6699；[37] Advanced Synthesis and Catalysis, 2016, vol.358, #15, p.2392-2397；[38] Journal of the American Chemical Society, 2016, vol.138, #36, p.11860-11871；[39] Beilstein Journal of Organic Chemistry, 2016, vol.12, p.2636-2643；[40] Chemistry - A European Journal, 2017, vol.23, #13, p.3062-3066；[41] Advanced Synthesis and Catalysis, 2017, vol.359, #11, p.1996-2000；[42] Green Chemistry, 2017, vol.19, #13, p.2925-2930；[43] Chemical Communications, 2017, vol.53, #54, p.7665-7668；[44] Organic and Biomolecular Chemistry, 2017, vol.15, #35, p.7369-7373；[45] Chemistry - A European Journal, 2018, vol.24, #71, p.18857-18862；[46] Chemical Communications (Cambridge, United Kingdom), 2018, vol.54, #96, p.13587-13590
路线2：镉配合物催化法
- 步骤：将溴苯衍生物（0.5mmol，1.0当量）、{(4,5-二氢-2-(4,5-二氢-4,4-二甲基恶唑-2-基)-4,4-二甲基-恶唑)CdCl}₂(μ-Cl)₂（19mg，0.05mmol，0.1当量）和氢氧化钾（19mg，0.5mmol，1.0当量）加入DMSO（0.5mL）中，110℃搅拌10分钟；加入烷基胺（1.0mmol，2.0当量），110℃搅拌数小时；粗反应混合物直接上硅胶柱色谱纯化得产物。
- 条件：以DMSO为溶剂，镉配合物为催化剂，氢氧化钾为碱，分两阶段反应（110℃各10分钟和数小时）。
- 收率：92%
- 参考文献：[1] Synlett, 2010, #6, p.939-943；[2] Inorganica Chimica Acta, 2015, vol.427, p.226-231；[3] Chemistry - A European Journal, 2017, vol.23, #39, p.9313-9318；[4] Chemistry - A European Journal, 2018, vol.24, #37, p.9269-9273；[5] Chemical Communications, 2014, vol.51, #2, p.334-337；[6] Journal of Organic Chemistry, 2004, vol.69, #19, p.6504-6506；[7] Synthetic Communications, 2001, vol.31, #7, p.987-992；[8] Journal of Organometallic Chemistry, 2012, vol.720, p.7-18,12；[9] Journal of Chemical Research, 2013, vol.37, #2, p.99-101；[10] Australian Journal of Chemistry, 2015, vol.68, #12, p.1890-1893
路线3：铜催化法
- 步骤：在Schlenk管中加入碘化铜（I）（0.20g，1.0mmol）和磷酸钾（4.25g，20.0mmol），抽真空氮气回填三次；依次加入2-丙醇（10.0mL）、乙二醇（1.11mL，20.0mmol）、1,2,3,4-四氢异喹啉（2.0mL，15mmol）和碘苯（1.12mL，10.0mmol）；85-90℃加热搅拌24小时，冷却后加二乙醚（20mL）和水（20mL），乙醚萃取（2×20mL），合并有机相用饱和食盐水洗涤、无水硫酸钠干燥，旋蒸除溶剂，硅胶柱色谱纯化（洗脱剂：乙酸乙酯/正己烷=1:20）得产物。
- 条件：以2-丙醇为溶剂，乙二醇为添加剂，碘化铜（I）为催化剂，磷酸钾为碱，85-90℃反应24小时，惰性气氛。
- 收率：75%
- 产物性质：黄色粘稠液体；TLC Rf=0.70（硅胶板，乙酸乙酯/正己烷=1:20）；1H NMR（400 MHz, CDCl3）δ:7.43-7.19（m,6H）,7.08（d,J=7.4Hz,2H）,6.92（t,J=6.5Hz,1H）,4.50（s,2H）,3.65（d,J=6.4Hz,2H）,3.08（d,J=5.7Hz,2H）；13C NMR（101 MHz, CDCl3）δ:150.66,134.99,134.58,129.32,128.64,126.66,126.44,126.14,118.78,115.26,50.85,46.65,29.25；HRMS-ESI m/z: [M+H]+计算值210.1277，实测值210.1269；IR（KBr）ν:3063,3028,2927,2813,1737,1662,1601,1500,1456,1386,1242,1036,931,752,695 cm-1。
- 参考文献：[1] Chemical Communications, 2017, vol.53, #93, p.12536-12539；[2] Australian Journal of Chemistry, 2015, vol.68, #12, p.1890-1893；[3] Advanced Synthesis and Catalysis, 2017, vol.359, #16, p.2832-2846；[4] Journal of Molecular Catalysis A: Chemical, 2017, vol.426, p.398-406；[5] Monatshefte fur Chemie, 2017, vol.148, #1, p.91-104
