Copper-Catalyzed and Indium-Mediated Methoxycarbonylation of Unactivated Alkyl Iodides with Balloon CO

被引:24
作者
Chen, Yanchi [1 ,2 ]
Su, Lei [1 ,2 ]
Gong, Hegui [1 ,2 ]
机构
[1] Shanghai Univ, Sch Mat Sci & Engn, Ctr Supramol Chem & Catalysis, 99 Shang Da Rd, Shanghai 200444, Peoples R China
[2] Shanghai Univ, Dept Chem, 99 Shang Da Rd, Shanghai 200444, Peoples R China
关键词
RADICAL-ADDITION; SATURATED ALCOHOLS; CARBON-MONOXIDE; CARBONYLATION; METAL; ALKOXYCARBONYLATION; COMPLEXES; PRECURSOR; REAGENTS; PD;
D O I
10.1021/acs.orglett.9b01573
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work emphasizes the synthesis of alkyl esters via Cu-catalyzed and In-mediated alkoxycarbonylation of unactivated alkyl iodides in the presence of In or InI. The reactions were suitable for the preparation of primary, secondary, and even tertiary alkyl esters, representing an exceptionally rare example for the creation of quaternary carbon centers upon formation of esters. The preliminary mechanistic studies indicated that alkyl radicals were involved, and Cu/In/CO played a cooperative role in the carbonylation event.
引用
收藏
页码:4689 / 4693
页数:5
相关论文
共 40 条
[1]   Recent advances in indium-promoted organic reactions [J].
Auge, Jacques ;
Lubin-Germain, Nadege ;
Uziel, Jacques .
SYNTHESIS-STUTTGART, 2007, (12) :1739-1764
[2]   A novel atom-transfer cyclisation catalysed by indium metal in halogenated solvents [J].
Bhatti, NH ;
Salter, MM .
TETRAHEDRON LETTERS, 2004, 45 (45) :8379-8382
[3]   Indium-mediated alkyl radical addition to (η6-arene)tricarbonylmanganese complexes in aqueous media [J].
Cao, LD ;
Shen, MH ;
Li, CZ .
ORGANOMETALLICS, 2005, 24 (24) :5983-5988
[4]   Cobalt-catalyzed photolytic methoxycarbonylation of bromoalkanes in the presence of a Lewis acid [J].
Cash, D ;
Combs, A ;
Dragojlovic, V .
TETRAHEDRON LETTERS, 2004, 45 (06) :1143-1145
[5]   Synthesis of Alkyl Indium Reagents by Using Unactivated Alkyl Chlorides and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions with Aryl Halides [J].
Chen, Bing-Zhi ;
Zhi, Man-Ling ;
Wang, Chuang-Xin ;
Chu, Xue-Qiang ;
Shen, Zhi-Liang ;
Loh, Teck-Peng .
ORGANIC LETTERS, 2018, 20 (07) :1902-1905
[6]   Copper-Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β-Borylenones [J].
Cheng, Li-Jie ;
Mankad, Neal P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) :10328-10332
[7]   Synthesis of Allylic Alcohols via Cu-Catalyzed Hydrocarbonylative Coupling of Alkynes with Alkyl Halides [J].
Cheng, Li-Jie ;
Islam, Shahidul M. ;
Mankad, Neal P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (03) :1159-1164
[8]   Cu-Catalyzed Hydrocarbonylative C-C Coupling of Terminal Alkynes with Alkyl Iodides [J].
Cheng, Li-Jie ;
Mankad, Neal P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (30) :10200-10203
[9]   Intermolecular alkyl radical addition to chiral N-acylhydrazones mediated by manganese carbonyl [J].
Friestad, GK ;
Qin, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9922-9923
[10]   Catalysts for cross-coupling reactions with non-activated alkyl halides [J].
Frisch, AC ;
Beller, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :674-688