Regioselective construction of 2-substituted indolines enabled by a rhodium-catalyzed decarboxylation-hydroacylation sequence

被引：0
|
作者：
Zhao, Jun [1 ,2 ]
Yang, Wen-Jing [1 ,2 ]
Lu, Yuan-Yi [1 ,2 ]
Teng, Yu [1 ,2 ]
Lu, Shi-Chao [3 ,4 ]
Li, Hong-Shuang [1 ,2 ]
机构：
[1] Shandong First Med Univ & Shandong Acad Med Sci, Sch Pharmaceut Sci, State Key Lab Adv Drug Delivery & Release Syst, Jinan 250117, Peoples R China
[2] Shandong First Med Univ & Shandong Acad Med Sci, Inst Mat Med, Jinan 250117, Peoples R China
[3] Chinese Acad Med Sci & Peking Union Med Coll, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[4] Chinese Acad Med Sci & Peking Union Med Coll, Beijing Key Lab Act Subst Discovery & Druggabil Ev, Inst Mat Med, Beijing 100050, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 19期
基金：
北京市自然科学基金;
关键词：
VINYL BENZOXAZINANONES; C-H; PALLADIUM; CYCLOADDITIONS; ISOMERIZATION; ANNULATIONS; ALDEHYDES; ALCOHOLS;
D O I：
10.1039/d4qo01234h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we describe the first rhodium(i)-catalyzed decarboxylative cyclization and hydroacylation of vinyl benzoxazinanones with chelating aldehydes, allowing a straightforward and efficient synthesis of 2-substituted indolines in moderate to good yields with excellent regioselectivity. Of note, the mechanistic proposal indicates that a new intermediate featuring eta 2-coordination may be in situ generated through a nucleophilic attack at the central carbon of the pi-allylmetal intermediate followed by reductive elimination. This study provides unique insights into the reactivity of pi-allylmetal species that can be used in hydrofunctionalization. Rhodium(i)-catalyzed sequential decarboxylation and hydroacylation of vinyl benzoxazinanones with chelating aldehydes for the highly regioselective synthesis of 2-substituted indolines via a new eta 2-Rh complex has been developed.
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页码：5495 / 5501
页数：7
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