钯碳催化剂

钯碳催化剂
	IUPAC名; Palladium; 钯
别名	钯碳，Pd/C，Pd-C
识别
CAS号	7440-05-3
PubChem	23938
SMILES	[Pd];
InChI	1S/Pd;
InChIKey	KDLHZDBZIXYQEI-UHFFFAOYSA-N
性质
化学式	Pd
摩尔质量	106.42 g·mol⁻¹
外观	黑色粉末
溶解性	溶于王水
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

钯碳催化剂（Palladium on carbon，Pd/C），通常称为钯碳，是一种用于催化剂的钯形式。^[1]金属负载在活性炭上，以使其表面积和活性最大化。

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用途

氢化

钯碳能用于有机合成中的催化氢化。包括还原胺化反应、^[2]羰基还原反应、硝基化合物的还原反应、^[3]^[4]亚胺和席夫碱的还原^[1]和脱苄基反应。

氢解

钯碳是氢解的常用催化剂。这种反应有助于脱保护策略。特别常见的氢解底物是苄基醚： ^[5]

其他不稳定的取代基也容易被该试剂裂解。^[6]

偶联反应

钯碳也用于偶联反应。包括铃木反应和施蒂勒反应。^[7]

制备

将氯化钯和盐酸与活性炭的悬浊液混合，然后用甲醛或氢气将钯(II)还原。^[8]^[8]钯负载通常在5%和10%之间。催化剂混合物应潮湿储存。

注意事项

在空气中密闭存放时很安全，但要远离溶剂和含硫、磷的化合物。在溶剂存在下，可能起火。在有机溶剂中使用时必须在氮气保护下进行。过滤时滤渣不能进行干燥。钯碳催化剂不能暴露于空气，容易着火，所以一般是用50%的湿钯碳。加料时必须用惰性气体保护，否则和溶剂蒸汽摩擦也会引起着火。^[9]

参见

钯黑
铂碳
二氧化铂
氧化铂铑
林德拉催化剂
雷尼镍
漆原镍

参考资料

[1]
Nishimura, Shigeo. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis 1st. New York: Wiley-Interscience. 2001: 34–38 [2022-04-14]. ISBN 9780471396987. （原始内容存档于2022-06-20）.
[2]
Romanelli, Michael G.; Becker, Ernest I. Ethylp-dimethylaminophenylacetate. Organic Syntheses. 1967, 47: 69. doi:10.15227/orgsyn.047.0069.
[3]
Smith, Michael B.; March, Jerry. March's Advanced Organic Chemistry 6th. John Wiley & Sons. 2007: 1816. ISBN 978-0-471-72091-1.
[4]
Ram, Siya; Ehrenkaufer, Richard E. A general procedure for mild and rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent. Tetrahedron Lett. 1984, 25 (32): 3415–3418. doi:10.1016/S0040-4039(01)91034-2. hdl:2027.42/25034 .
[5]
Smith, Amos B.; Zhu, Wenyu; Shirakami, Shohei; Sfouggatakis, Chris; Doughty, Victoria A.; Bennett, Clay S.; Sakamoto, Yasuharu. Total Synthesis of (+)-Spongistatin 1. An Effective Second-Generation Construction of an Advanced EF Wittig Salt, Fragment Union, and Final Elaboration. Organic Letters. 2003-03-01, 5 (5): 761–764. ISSN 1523-7060. PMID 12605509. doi:10.1021/ol034037a.
[6]
Musliner, Walter J.; Gates, Jr, John W. Dehydroxylation of Phenols; Hydrogenolysis of Phenolic Ethers: Biphenyl. Organic Syntheses. 1971, 51: 82. doi:10.15227/orgsyn.051.0082.
[7]
Liebeskind, Lanny S.; Peña-Cabrera, Eduardo. Stille couplings catalyzed by palladium-on-carbon with CuI as a co-catalyst: synthesis of 2-(4'-Acetylhenyl)thiophene. Organic Syntheses. 2000, 77: 138. doi:10.15227/orgsyn.077.0135.
[8]
Mozingo, Ralph. Palladium catalysts. Organic Syntheses. 1946, 26: 77–82. PMID 20280763. doi:10.15227/orgsyn.026.0077.
[9]
胡跃飞等编著. 现代有机合成试剂——性质、制备和反应. 北京: 化学工业出版社. 2006年4月: 5–6. ISBN 7-5025-8542-7.

[Shigeo-1] [1]
Nishimura, Shigeo. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis 1st. New York: Wiley-Interscience. 2001: 34–38 [2022-04-14]. ISBN 9780471396987. （原始内容存档于2022-06-20）.

[2] [2]
Romanelli, Michael G.; Becker, Ernest I. Ethylp-dimethylaminophenylacetate. Organic Syntheses. 1967, 47: 69. doi:10.15227/orgsyn.047.0069.

[March-3] [3]
Smith, Michael B.; March, Jerry. March's Advanced Organic Chemistry 6th. John Wiley & Sons. 2007: 1816. ISBN 978-0-471-72091-1.

[4] [4]
Ram, Siya; Ehrenkaufer, Richard E. A general procedure for mild and rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent. Tetrahedron Lett. 1984, 25 (32): 3415–3418. doi:10.1016/S0040-4039(01)91034-2. hdl:2027.42/25034 .

[5] [5]
Smith, Amos B.; Zhu, Wenyu; Shirakami, Shohei; Sfouggatakis, Chris; Doughty, Victoria A.; Bennett, Clay S.; Sakamoto, Yasuharu. Total Synthesis of (+)-Spongistatin 1. An Effective Second-Generation Construction of an Advanced EF Wittig Salt, Fragment Union, and Final Elaboration. Organic Letters. 2003-03-01, 5 (5): 761–764. ISSN 1523-7060. PMID 12605509. doi:10.1021/ol034037a.

[6] [6]
Musliner, Walter J.; Gates, Jr, John W. Dehydroxylation of Phenols; Hydrogenolysis of Phenolic Ethers: Biphenyl. Organic Syntheses. 1971, 51: 82. doi:10.15227/orgsyn.051.0082.

[7] [7]
Liebeskind, Lanny S.; Peña-Cabrera, Eduardo. Stille couplings catalyzed by palladium-on-carbon with CuI as a co-catalyst: synthesis of 2-(4'-Acetylhenyl)thiophene. Organic Syntheses. 2000, 77: 138. doi:10.15227/orgsyn.077.0135.

[#1-8] [8]
Mozingo, Ralph. Palladium catalysts. Organic Syntheses. 1946, 26: 77–82. PMID 20280763. doi:10.15227/orgsyn.026.0077.

[9] [9]
胡跃飞等编著. 现代有机合成试剂——性质、制备和反应. 北京: 化学工业出版社. 2006年4月: 5–6. ISBN 7-5025-8542-7.

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