Copper-catalyzed C(sp3)-H alkylation of fluorene with primary and secondary alcohols using a borrowing hydrogen method

被引：2
作者：
Saha, Ratnakar [1 ]
Maharana, Suraj Kumar [1 ]
Jana, Narayan Ch. [1 ]
Bagh, Bidraha [1 ]
机构：
[1] Natl Inst Sci Educ & Res NISER, OCC Homi Bhabha Natl Inst, Sch Chem Sci, Khurja 752050, Odisha, India
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 74期
关键词：
ALPHA-ALKYLATION; N-ALKYLATION; KETONES; COMPLEXES; PHOTOLUMINESCENCE; SULFONAMIDES;
D O I：
10.1039/d4cc03310h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Despite the limited success of copper-catalyzed alkylations, (NNS)CuCl proved to be an effective catalyst for the sp(3) C-H alkylation of fluorene with alcohols. Various primary alcohols and challenging secondary alcohols were successfully used. The practical applicability of the method was effectively tested with several post-functionalization reactions. This copper-catalyzed alkylation of fluorene involved a borrowing hydrogen mechanism.
引用
收藏
页码：10144 / 10147
页数：4
相关论文
共 48 条
[1]   Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization [J].
Achar, Tapas Kumar ;
Maiti, Sudip ;
Jana, Sadhan ;
Maiti, Debabrata .
ACS CATALYSIS, 2020, 10 (23) :13748-13793
[2]   C-Alkylation by Phenalenyl-Based Molecule via a Borrowing Hydrogen Pathway [J].
Banik, Ananya ;
Datta, Paramita ;
Mandal, Swadhin K. .
ORGANIC LETTERS, 2023, :1305-1309
[3]   Catalytic Conversion of Nonfood Woody Biomass Solids to Organic Liquids [J].
Barta, Katalin ;
Ford, Peter C. .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1503-1512
[4]   Ligand-assisted nickel catalysis enabling sp3 C-H alkylation of 9H-fluorene with alcohols [J].
Biswas, Ayanangshu ;
Bains, Amreen K. ;
Adhikari, Debashis .
CATALYSIS SCIENCE & TECHNOLOGY, 2022, 12 (13) :4211-4216
[5]   Osmium Catalyst for the Borrowing Hydrogen Methodology: α-Alkylation of Arylacetonitriles and Methyl Ketones [J].
Buil, Maria L. ;
Esteruelas, Miguel A. ;
Herrero, Juana ;
Izquierdo, Susana ;
Pastor, Isidro M. ;
Yus, Miguel .
ACS CATALYSIS, 2013, 3 (09) :2072-2075
[6]   Ruthenium and osmium complexes in C-C bond-forming reactions by borrowing hydrogen catalysis [J].
Chelucci, Giorgio .
COORDINATION CHEMISTRY REVIEWS, 2017, 331 :1-36
[7]   Synthesis, Characterization, and Photophysical Properties of Heteroleptic Copper(I) Complexes with Functionalized 3-(2'-PyridyI)-1,2,4-triazole Chelating Ligands [J].
Chen, Jing-Lin ;
Cao, Xing-Fu ;
Wang, Jin-Yun ;
He, Li-Hua ;
Liu, Zong-Yong ;
Wen, He-Rui ;
Chen, Zhong-Ning .
INORGANIC CHEMISTRY, 2013, 52 (17) :9727-9740
[8]   Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions [J].
Cook, Adam ;
Newman, Stephen G. .
CHEMICAL REVIEWS, 2024, 124 (09) :6078-6144
[9]   Copper-Catalyzed N-Alkylation of Sulfonamides with Benzylic Alcohols: Catalysis and Mechanistic Studies [J].
Cui, Xinjiang ;
Shi, Feng ;
Tse, Man Kin ;
Goerdes, Dirk ;
Thurow, Kerstin ;
Beller, Matthias ;
Deng, Youquan .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) :2949-2958
[10]   Iron-Catalyzed α-Alkylation of Ketones with Alcohols [J].
Elangovan, Saravanakumar ;
Sortais, Jean-Baptiste ;
Beller, Matthias ;
Darcel, Christophe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) :14483-14486
12345