鈀碳催化劑

鈀碳催化劑
	IUPAC名; Palladium; 鈀
別名	鈀碳，Pd/C，Pd-C
識別
CAS號	7440-05-3
PubChem	23938
SMILES	[Pd];
InChI	1S/Pd;
InChIKey	KDLHZDBZIXYQEI-UHFFFAOYSA-N
性質
化學式	Pd
摩爾質量	106.42 g·mol⁻¹
外觀	黑色粉末
溶解性	溶於王水
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

鈀碳催化劑（Palladium on carbon，Pd/C），通常稱為鈀碳，是一種用於催化劑的鈀形式。^[1]金屬負載在活性炭上，以使其表面積和活性最大化。

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用途

氫化

鈀碳能用於有機合成中的催化氫化。包括還原胺化反應、^[2]羰基還原反應、硝基化合物的還原反應、^[3]^[4]亞胺和席夫鹼的還原^[1]和脫苄基反應。

氫解

鈀碳是氫解的常用催化劑。這種反應有助於脫保護策略。特別常見的氫解底物是苄基醚： ^[5]

其他不穩定的取代基也容易被該試劑裂解。^[6]

偶聯反應

鈀碳也用於偶聯反應。包括鈴木反應和施蒂勒反應。^[7]

製備

將氯化鈀和鹽酸與活性炭的懸濁液混合，然後用甲醛或氫氣將鈀(II)還原。^[8]^[8]鈀負載通常在5%和10%之間。催化劑混合物應潮濕儲存。

注意事項

在空氣中密閉存放時很安全，但要遠離溶劑和含硫、磷的化合物。在溶劑存在下，可能起火。在有機溶劑中使用時必須在氮氣保護下進行。過濾時濾渣不能進行乾燥。鈀碳催化劑不能暴露於空氣，容易着火，所以一般是用50%的濕鈀碳。加料時必須用惰性氣體保護，否則和溶劑蒸汽摩擦也會引起着火。^[9]

參見

鈀黑
鉑碳
二氧化鉑
氧化鉑銠
林德拉催化劑
雷尼鎳
漆原鎳

參考資料

[1]
Nishimura, Shigeo. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis 1st. New York: Wiley-Interscience. 2001: 34–38 [2022-04-14]. ISBN 9780471396987. （原始內容存檔於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]
胡躍飛等編著. 现代有机合成试剂——性质、制备和反应. 北京: 化學工業出版社. 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. （原始內容存檔於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]
胡躍飛等編著. 现代有机合成试剂——性质、制备和反应. 北京: 化學工業出版社. 2006年4月: 5–6. ISBN 7-5025-8542-7.

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