Unknown

Dataset Information

0

Exploring Possible Surrogates for Kobayashi's Aryne Precursors.


ABSTRACT: A class of aryne precursors, that is, 2-(trimethylsilyl)aryl 4-chlorobenzenesulfonates, has been developed through well-established synthetic routes, which allow the formation of arynes under relatively mild conditions. All the aryne precursors were obtained from phenols and 4-chlorobenzenesulfonyl chloride, an inexpensive and easy-to-handle reagent with relatively low toxicity, and subjected to nucleophilic addition reactions, providing addition products in yields of 24 to 92%, and to cycloaddition reactions, affording cycloadducts in yields up to 80%. This work provides interesting insights into the mechanisms of aryne generation. In addition, 2-(trimethylsilyl)phenyl 4-chlorobenzenesulfonate was successfully employed in the total synthesis of (±)-aporphine.

SUBMITTER: Muraca ACA 

PROVIDER: S-EPMC7017410 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

altmetric image

Publications

Exploring Possible Surrogates for Kobayashi's Aryne Precursors.

Muraca Ana Carolina A ACA   Raminelli Cristiano C  

ACS omega 20200131 5


A class of aryne precursors, that is, 2-(trimethylsilyl)aryl 4-chlorobenzenesulfonates, has been developed through well-established synthetic routes, which allow the formation of arynes under relatively mild conditions. All the aryne precursors were obtained from phenols and 4-chlorobenzenesulfonyl chloride, an inexpensive and easy-to-handle reagent with relatively low toxicity, and subjected to nucleophilic addition reactions, providing addition products in yields of 24 to 92%, and to cycloaddi  ...[more]

Similar Datasets

| S-EPMC5020908 | biostudies-literature
| S-EPMC5501486 | biostudies-literature
| S-EPMC4600243 | biostudies-literature
| S-EPMC7201866 | biostudies-literature
| S-EPMC7097847 | biostudies-literature
| S-EPMC9299019 | biostudies-literature
| S-EPMC4221504 | biostudies-literature
| S-EPMC6589797 | biostudies-literature
| S-EPMC3583249 | biostudies-other
| S-EPMC2819077 | biostudies-literature