Lewis Acid-Catalyzed Sulfur Fluoride Exchange

被引:2
|
作者
Yassa, Theodore D. [1 ]
Fang, Yuxin [1 ]
Ravelo, Lana K. [1 ]
Anand, Sanah [1 ]
Arora, Saira [1 ]
Ball, Nicholas D. [1 ]
机构
[1] Pomona Coll, Dept Chem, Claremont, CA 91711 USA
基金
美国国家卫生研究院;
关键词
SULFONYL FLUORIDES; SUFEX; SULFONAMIDES;
D O I
10.1021/acs.orglett.4c03726
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method uses metal Lewis acids as catalysts to convert sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides with silyl amines into S-N bond-containing compounds via sulfur fluoride exchange. The reaction successfully employs Ca(NTf2)2 as a catalyst to form sulfonamides, sulfamates, and sulfamides using in situ-generated or commercially available silyl amines in 35-99% yields. Other metal Lewis acids are also demonstrated to be catalysts in SuFEx, forming sulfonamides and sulfamates in yields comparable to those of Ca(NTf2)2.
引用
收藏
页码:9897 / 9902
页数:6
相关论文
共 50 条
  • [1] Lewis acid-catalyzed [4
    Sun, Yuwen
    Wang, Zhaoshan
    Wu, Shufang
    Zhang, Yuchen
    Shi, Feng
    GREEN SYNTHESIS AND CATALYSIS, 2022, 3 (01): : 84 - 88
  • [2] INTRAMOLECULAR LEWIS ACID-CATALYZED ALKYLATIONS
    EVANS, EH
    HEWSON, AT
    WADSWORTH, AH
    SYNTHETIC COMMUNICATIONS, 1985, 15 (03) : 243 - 247
  • [3] Lewis acid-catalyzed synthesis of aziridines
    Casarrubios, L
    Perez, JA
    Brookhart, M
    Templeton, JL
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24): : 8358 - 8359
  • [4] LEWIS ACID-CATALYZED PREPARATION OF TETRAMETHYLHEXATHIOADAMANTANE
    GIAM, CS
    TABOR, RL
    GOODWIN, TE
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1981, 13 (02) : 134 - 136
  • [5] LEWIS ACID-CATALYZED REARRANGEMENT OF TRITERPENOIDS
    CHATTERJEE, A
    MUKHOPADHYAY, S
    CHATTOPADHYAY, K
    TETRAHEDRON, 1976, 32 (24) : 3051 - 3053
  • [6] THE ACID-CATALYZED REACTIONS OF PENTAMETHYLBENZYL FLUORIDE
    LEE, SK
    HAGAMAN, EW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 144 - ORGN
  • [7] A LEWIS ACID-CATALYZED REARRANGEMENT OF ALLENOL ETHERS
    RICCI, A
    DEGL'INNOCENTI, A
    CAPPERUCCI, A
    FAGGI, C
    SECONI, G
    FAVARETTO, L
    SYNLETT, 1990, (08) : 471 - 473
  • [8] Lewis and Bronsted acid-catalyzed allylsilane oligomerization
    Wigman, Benjamin
    Franz, Annaliese
    Armstrong, Brittany
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [9] LEWIS ACID-CATALYZED REARRANGEMENTS OF NITROXIDE RADICALS
    CAZIANIS, CT
    EATON, DR
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (13): : 2463 - 2470
  • [10] ON THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF IMINES WITH A SILOXYDIENE
    KERWIN, JF
    DANISHEFSKY, S
    TETRAHEDRON LETTERS, 1982, 23 (37) : 3739 - 3742