Chan-Lam Coupling_Chan-Lam耦合

这个反应允许芳基碳杂原子键的形成，通过氧化耦合的硼酸，锡或硅氧烷与空气中的N-H或O-H含化合物。底物包括酚类、胺类、苯胺类、酰胺类、酰亚胺类、脲类、氨基甲酸酯类和磺胺类。反应是由化学计量量的铜（II）或催化量的铜催化剂诱导的，该催化剂被大气氧或另一种初级氧化剂重新氧化。

Chan-lam耦合可以在室温下在空气中进行，这使得它比Buchwald-Hartwig交叉耦合具有一定的优势。

Chan-lam耦合机理

与化学计量量的铜（II）的反应也受到氧气的促进，因为从铜（III）中还原性消除更快。

Recent Literature 近期文献

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
J. C. Vantourout, H. N. Miras, A. Isidro-Llobet, S. Sproules, A. J. B. Watson, J. Am. Chem. Soc., 2017, 139, 4769-4779.

Ligand- and Base-Free Copper(II)-Catalyzed C-N Bond Formation: Cross-Coupling Reactions of Organoboron Compounds with Aliphatic Amines and Anilines
T. D. Quach, R. A. Batey, Org. Lett., 2003, 5, 4397-4400.

Copper(II)-Catalyzed Ether Synthesis from Aliphatic Alcohols and Potassium Organotrifluoroborate Salts
T. D. Quach, R. A. Batey, Org. Lett., 2003, 5, 1381-1384.

A Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid proceeds in air as sole oxidant and offers a strategy for replacing toxic, electrophilic alkylating reagents. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation.
C. E. Jacobson, N. Martinez-Muñoz, D. J. Gorin, J. Org. Chem., 2015, 80, 7305-7310.

Copper-Catalyzed N- and O-Alkylation of Amines and Phenols using Alkylborane Reagents
S. Sueki, Y. Kuninobu, Org. Lett., 2013, 15, 1544-1547.

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
J. C. Vantourout, R. P. Law, A. Isidro-Llobet, S. J. Atkinson, A. J. B. Watson, J. Org. Chem., 2016, 81, 3942-3950.

Selective Formation of Secondary Amides via the Copper-Catalyzed Cross-Coupling of Alkylboronic Acids with Primary Amides
S. A. Rossi, K. W. Shimkin, Q. Xu, L. M. Mori-Quiroz, D. A. Watson, Org. Lett., 2013, 15, 2314-2317.

An Efficient Base-Free N-Arylation of Imidazoles and Amines with Arylboronic Acids Using Copper-Exchanged Fluorapatite
M. L. Kantam, G. T. Venkanna, C. Sridhar, B. Sreedhar, B. M. Choudary, J. Org. Chem., 2006, 71, 9522-9524.

Nickel-Mediated N-Arylation with Arylboronic Acids: An Avenue to Chan-Lam Coupling
D. S. Raghuvanshi, A. K. Gupta, K. N. Singh, Org. Lett., 2012, 14, 4326-4329.

Synthesis of N-Aryl Amides by Ligand-Free Copper-Catalyzed ipso-Amidation of Arylboronic Acids with Nitriles
Y. Qiao, G. Li, S. Liu, Y. Yangkai, J. Tu, F. Xu, Synthesis, 2017, 49, 1834-1838.

A Synthetic Approach to N-Aryl Carbamates via Copper-Catalyzed Chan-Lam Coupling at Room Temperature
S.-Y. Moon, U. Bin Kim, D.-B. Sung, W.-S. Kim, J. Org. Chem., 2015, 80, 1856-1865.

Microwave-assisted conditions enabled a simple, rapid, one-pot synthesis of arylaminomethyl acetylenes in very good yields using arylboronic acids, aqueous ammonia, propargyl halides, copper(I) oxide and water as the solvent within ten minutes.
Y. Jiang, S. Huang, Synlett, 2014, 25, 407-410.

One-Pot Approach to 1,2-Disubstituted Indoles via Cu(II)-Catalyzed Coupling/Cyclization under Aerobic Conditions and Its Application for the Synthesis of Polycyclic Indoles
J. Gao, Y. Shao, J. Zhu, H. Mao, X. Wang, X. Lv, J. Org. Chem., 2014, 79, 9000-9008.

Synthesis of Diaryl Ethers through the Copper-Promoted Arylation of Phenols with Arylboronic Acids. An Expedient Synthesis of Thyroxine
D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Letters, 1998, 39, 2937-2940.

Cu(OTf)₂-Mediated Chan-Lam Reaction of Carboxylic Acids to Access Phenolic Esters
L. Zhang, G. Zhang, M. Zhang, J. Cheng, J. Org. Chem., 2010, 75, 7472-7474.

Copper-Catalyzed Formamidation of Arylboronic Acids: Direct Access to Formanilides
V. P. Srivastava, D. K. Yadav, A. K. Yadav, G. Watal, L. D. S. Yadav, Synlett, 2013, 24, 1423-1427.

Copper-Catalyzed N-Arylation of Sulfonamides with Boronic Acids in Water under Ligand-Free and Aerobic Conditions
M. Nasrollahzadeh, A. Ehsani, M. Maham, Synlett, 2014, 25, 505-508.

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Chan-Lam耦合_Chan-Lam Coupling

Chan-Lam Coupling_Chan-Lam耦合