Nickel-Catalyzed Decarbonylative Borylation and Silylation of Esters

被引:174
作者
Pu, Xinghui [1 ]
Hu, Jiefeng [1 ]
Zhao, Yue [1 ]
Shi, Zhuangzhi [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Collaborat Innovat Ctr Chem Life Sci, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China
关键词
nickel; borylation; silylation; esters; decarbonylation; C-H BONDS; CROSS-COUPLING REACTIONS; CARBON-CYANO BONDS; O BOND; DIRECTING GROUP; ARYL CHLORIDES; ORGANOBORON COMPOUNDS; REDUCTIVE CLEAVAGE; GRIGNARD-REAGENTS; DIRECT ALKYLATION;
D O I
10.1021/acscatal.6b01956
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The nickel-catalyzed direct borylation and silylation of phenolic esters has been established. The key to this highly efficient acyl C-O bond borylative and silylative cleavage depends on the appropriate choice of different ligands and additives in the presence of nickel catalyst. Both transformations exhibit good functional group compatibility and can serve as powerful synthetic tools for late-stage functionalization of complex compounds. The elucidation of key mechanistic features of this newly developed acyl C-O bond activation in esters was confirmed by two well-characterized organonickel(II) intermediates.
引用
收藏
页码:6692 / 6698
页数:7
相关论文
共 112 条
[1]   Ni-Catalyzed Reduction of Inert C-O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups [J].
Alvarez-Bercedo, Paula ;
Martin, Ruben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (49) :17352-17353
[2]   Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].
Amaike, Kazuma ;
Muto, Kei ;
Yamaguchi, Junichiro ;
Itami, Kenichiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576
[3]  
Bains W, 2003, CURR OPIN DRUG DISC, V6, P526
[4]   Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates [J].
Basch, Corey H. ;
Cobb, Kelsey M. ;
Watson, Mary P. .
ORGANIC LETTERS, 2016, 18 (01) :136-139
[5]   Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies [J].
Billingsley, Kelvin L. ;
Barder, Timothy E. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5359-5363
[6]   Reductive Cleavage of the Csp2-Csp3 Bond of Secondary Benzyl Alcohols: Rhodium Catalysis Directed by N-Containing Groups [J].
Chen, Kang ;
Li, Hu ;
Lei, Zhi-Quan ;
Li, Yang ;
Ye, Wen-He ;
Zhang, Li-Sheng ;
Sun, Jian ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) :9851-9855
[7]   Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C-O Bonds with Silanes: Ruling out a Classical Ni(0)/Ni(II) Catalytic Couple and Evidence for Ni(I) Intermediates [J].
Cornella, Josep ;
Gomez-Bengoa, Enrique ;
Martin, Ruben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (05) :1997-2009
[8]   Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage [J].
Correa, Arkaitz ;
Martin, Ruben .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (20) :7253-7256
[9]   Palladium-catalyzed silylation of aryl bromides leading to functionalized aryldimethylsilanols [J].
Denmark, SE ;
Kallemeyn, JM .
ORGANIC LETTERS, 2003, 5 (19) :3483-3486
[10]   Iron-Catalyzed C-H Borylation of Arenes [J].
Dombray, Thomas ;
Werncke, C. Gunnar ;
Jiang, Shi ;
Grellier, Mary ;
Vendier, Laure ;
Bontemps, Sebastien ;
Sortais, Jean-Baptiste ;
Sabo-Etienne, Sylviane ;
Darcel, Christophe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (12) :4062-4065