Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp3C-P bonds

被引:6
作者
Li, Qiang [1 ]
Zhao, Chang-Qiu [1 ]
Chen, Tieqiao [2 ]
Han, Li-Biao [2 ,3 ]
机构
[1] Liaocheng Univ, Coll Chem & Chem Engn, 1 Hunan Rd, Liaocheng 252059, Shandong, Peoples R China
[2] Hainan Univ, Key Lab Minist Educ Adv Mat Trop Isl Resources, Hainan Prov Key Lab Fine Chem, Hainan Prov Fine Chem Engn Res Ctr, Haikou 570228, Hainan, Peoples R China
[3] Zhejiang Yanfan New Mat Co Ltd, Shangyu 312369, Zhejiang, Peoples R China
关键词
DEHYDROGENATIVE-COUPLING REACTIONS; RADICAL TANDEM CYCLIZATION; REGIOSELECTIVE PHOSPHONATION; ARYLBORONIC ACIDS; CATALYTIC AMOUNTS; EFFICIENT; FUNCTIONALIZATION; ACTIVATION; VERSATILE; AMINES;
D O I
10.1039/d2ra02812c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct phosphorylation of benzylic C-H bonds was achieved in a biphasic system under transition metal-free conditions. A selective radical/radical sp(3)C-H/P(O)-H cross coupling was proposed, and various substituted toluenes were applicable. The transformation provided a promising method for constructing sp(3)C-P bonds.
引用
收藏
页码:18441 / 18444
页数:4
相关论文
共 102 条
[1]   Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds [J].
Ackermann, L ;
Born, R ;
Spatz, JH ;
Althammer, A ;
Gschrei, CJ .
PURE AND APPLIED CHEMISTRY, 2006, 78 (02) :209-214
[2]   CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164
[3]   Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C-H bonds: synthesis of α-aminophosphonates under aerobic conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
TETRAHEDRON LETTERS, 2012, 53 (12) :1456-1459
[4]   Phenylphosphonic acid functionalized poly [aryloxyphosphazenes] [J].
Allcock, HR ;
Hofmann, MA ;
Ambler, CM ;
Morford, RV .
MACROMOLECULES, 2002, 35 (09) :3484-3489
[5]   Aryl Radical Selectivity in Biphasic Systems [J].
Altmann, Lisa-Marie ;
Fuerst, Michael C. D. ;
Gans, Eva I. ;
Zantop, Viviane ;
Pratsch, Gerald ;
Heinrich, Markus R. .
ORGANIC LETTERS, 2020, 22 (02) :479-482
[6]   Microwave-Promoted Palladium(II)-Catalyzed C-P Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates [J].
Andaloussi, Mounir ;
Lindh, Jonas ;
Savmarker, Jonas ;
Sjoberg, Per J. R. ;
Larhed, Mats .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :13069-13074
[7]  
Arbusow B.A., 1964, PURE APPL CHEM, V9, P307
[8]   Catalytic synthesis of phosphines and related compounds [J].
Baillie, C ;
Xiao, JL .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (05) :477-514
[9]   Radical-initiated functionalization of methane and ethane in fuming sulfuric acid [J].
Basickes, N ;
Hogan, TE ;
Sen, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13111-13112
[10]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126