B(C6F5)3-Catalyzed Dehydrogenation of Pyrrolidines to Form Pyrroles

被引：6

作者：

Alvarez-Montoya, Ana ^{[1
]}

Gillions, Joseph P. ^{[1
]}

Winfrey, Laura ^{[1
]}

Hawker, Rebecca R. ^{[1
]}

Singh, Kuldip ^{[1
]}

Ortu, Fabrizio ^{[1
]}

Fu, Yukang ^{[2
]}

Li, Yang ^{[2
]}

Pulis, Alexander P. ^{[1
]}

机构：

[1] Univ Leicester, Sch Chem, Leicester LE1 7RH, England

[2] Dalian Univ Technol, Sch Chem Engn, 2 Linggong Rd, Dalian 116024, Peoples R China

来源：

ACS CATALYSIS | 2024年 / 14卷 / 07期

基金：

英国工程与自然科学研究理事会; 中国国家自然科学基金;

关键词：

dehydrogenation; pyrrolidines; pyrroles; N-heterocycles; catalysis; boranes; METAL-FREE HYDROGENATION; N-HETEROCYCLES; ACID; OXIDATION; AMINES; POLYMERIZATION; AROMATIZATION; REACTIVITY; CLEAVAGE;

D O I：

10.1021/acscatal.3c05444

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Pyrroles are important N-heterocycles found in medicines and materials. The formation of pyrroles from widely accessible pyrrolidines is a potentially attractive strategy but is an underdeveloped approach due to the sensitivity of pyrroles to the oxidative conditions required to achieve such a transformation. Herein, we report a catalytic approach that employs commercially available B(C6F5)(3) in an operationally simple procedure that allows pyrrolidines to serve as direct synthons for pyrroles. Mechanistic studies have revealed insights into borane-catalyzed dehydrogenative processes.

引用

页码：4856 / 4864

页数：9

共 50 条

[21] B(C6F5)3-Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes
Porwal, Digvijay
Oestreich, Martin
SYNTHESIS-STUTTGART, 2017, 49 (20): : 4698 - 4702
[22] B(C6F5)3-catalyzed transfer hydrogenations of imines with Hantzsch esters
Wang, Qiaotian
Chen, Jingjing
Feng, Xiangqing
Du, Haifeng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (09) : 1448 - 1451
[23] B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates
Blackwell, JM
Sonmor, ER
Scoccitti, T
Piers, WE
ORGANIC LETTERS, 2000, 2 (24) : 3921 - 3923
[24] B(C6F5)3-catalyzed hydrogermylation of enones: a facile route to germacycles
Xiong, Jiangkun
Yan, Maying
Jin, Lvnan
Song, Weihong
Xiao, Lei
Xu, Dong
Zhai, Chunyang
Stephan, Douglas W.
Guo, Jing
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (40) : 8098 - 8101
[25] B(C6F5)3-catalyzed metal-free hydrogenation of naphthylamines
Li, Gen
Liu, Yongbing
Du, Haifeng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2875 - 2878
[26] B(C6F5)3-catalyzed allylation of secondary benzyl acetates with allylsilanes
Rubin, M
Gevorgyan, V
ORGANIC LETTERS, 2001, 3 (17) : 2705 - 2707
[27] Studies on the mechanism of B(C6F5)3-catalyzed hydrosilation of carbonyl functions
Parks, DJ
Blackwell, JM
Piers, WE
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 3090 - 3098
[28] B(C6F5)3-Catalyzed Ring Opening and Isomerization of Unactivated Cyclopropanes
Zhang, Zi-Yu
Liu, Zhi-Yun
Guo, Rui-Ting
Zhao, Yu-Quan
Li, Xiang
Wang, Xiao-Chen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) : 4028 - 4032
[29] Selective B(C6F5)3-Catalyzed Reactions of α-Diazoesters with Heterocycles and Alkenes
Darmandeh, Heidar
Gessner, Viktoria H.
CHEM, 2020, 6 (09): : 2129 - 2131
[30] B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
Basak, Shyam
Alvarez-Montoya, Ana
Winfrey, Laura
Melen, Rebecca L.
Morrill, Louis C.
Pulis, Alexander P.
ACS CATALYSIS, 2020, 10 (08): : 4835 - 4840

← 1 2 3 4 5 →