Sulfonylation of Propargyl Alcohols with Sulfinamides for the Synthesis of Allenyl Sulfones

被引：9

作者：

Zou, Fei-Fei ^{[1
]}

Luo, Zhen ^{[1
]}

Yang, Yu-Ting ^{[1
]}

Zhuang, Xin ^{[1
]}

Hong, Chuan-Ming ^{[1
]}

Liu, Zheng-Qiang ^{[1
]}

Li, Wan-Fang ^{[2
]}

Li, Qing-Hua ^{[1
]}

Liu, Tang-Lin ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

[2] Univ Shanghai Sci & Technol, Coll Sci, Shanghai 200093, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 22期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; T-BUTYLSULFINAMIDE; REARRANGEMENT; LEWIS; ISOMERIZATION; BRASSINOLIDE; CHEMISTRY; EFFICIENT; SOLVENTS;

D O I：

10.1021/acs.joc.2c01495

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regio-and chemoselective sulfonylation of propargyl alcohols with sulfinamides in 1,1,1,3,3,3-hexafluoroisopro-panol (HFIP) was developed. It provided straightforward and mild access to multi-substituted allenyl sulfones by using sulfinamides as the sulfonyl sources. This transformation was promoted by HFIP and did not require any catalysts or oxidants, which allowed for the successful conversion of various tertiary and secondary propargyl alcohols into allenyl sulfones in high yields.

引用

页码：15061 / 15070

页数：10

共 50 条

[41] α-chlorovinylation:: Synthesis of 2-chloropropenyl and propargyl alcohols
Falck, JR
Barma, DK
Mioskowski, C
Schlama, T
TETRAHEDRON LETTERS, 1999, 40 (11) : 2091 - 2094
[42] Asymmetric synthesis of propargyl alcohols by alkynylzinc additions.
Pu, L
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U149 - U149
[43] A CONVENIENT SYNTHESIS OF SUBSTITUTED PROPARGYL ALCOHOLS AND TERMINAL ACETYLENES
BUMAGIN, NA
PONOMARYOV, AB
BELETSKAYA, IP
SYNTHESIS-STUTTGART, 1984, (09): : 728 - 729
[44] Synthesis and neurotropic activity of silyl propargyl alcohols and sulfides
Abele, R
Zvejniece, L
Abele, E
Rubina, K
Arsenyan, P
Vandish, M
Pudova, O
Dambrova, M
Domracheva, I
Shestakova, I
Popelis, J
Lukevics, E
APPLIED ORGANOMETALLIC CHEMISTRY, 2004, 18 (04) : 181 - 186
[45] AN EFFECTIVE, PRACTICAL METHOD FOR THE SYNTHESIS OF CHIRAL PROPARGYL ALCOHOLS
YADAV, JS
DESHPANDE, PK
SHARMA, GVM
TETRAHEDRON, 1990, 46 (20) : 7033 - 7046
[46] Facile synthesis of vinyl sulfones from β-bromo alcohols
Lee, JW
Lee, CW
Jung, JH
Oh, DY
SYNTHETIC COMMUNICATIONS, 2000, 30 (16) : 2897 - 2902
[47] Visible-Light-Induced Chemoselective Synthesis of α-Chloro and Vinyl Sulfones by Sulfonylation of Alkenes
Niu, Teng-fei
Lin, Dan
Xue, Lin-shuang
Jiang, Ding-yun
Ni, Bang-qing
SYNLETT, 2018, 29 (03) : 364 - 368
[48] SULFONYLATION OF ORGANOMETALLIC REAGENTS WITH ARENESULFONYL FLUORIDES - A SIMPLE ONE-STEP SYNTHESIS OF SULFONES
FRYE, LL
SULLIVAN, EL
CUSACK, KP
FUNARO, JM
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02): : 697 - 701
[49] Thermodynamically favored aldol reaction of propargyl or allenyl esters: Regioselective synthesis of carbinol allenoates
Xu, Bo
Hammond, Gerald B.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) : 689 - 692
[50] Synthesis of metallacyclobutenes of late transition metals via nucleophilic addition of allenyl or propargyl complexes
Cheng, YC
Chen, YK
Huang, TM
Yu, CI
Lee, GH
Wang, Y
Chen, JT
ORGANOMETALLICS, 1998, 17 (14) : 2953 - 2957

← 1 2 3 4 5 →