Rhodium(III)-Catalyzed Directed C-H Dienylation of Anilides with Allenes Leads to Highly Conjugated Systems

Chiranjit Ghosh; Prajyot Jayadev Nagtilak; Manmohan Kapur

doi:10.1021/acs.orglett.9b00958

Rhodium(III)-Catalyzed Directed C-H Dienylation of Anilides with Allenes Leads to Highly Conjugated Systems

Org Lett. 2019 May 3;21(9):3237-3241. doi: 10.1021/acs.orglett.9b00958. Epub 2019 Apr 18.

Authors

Chiranjit Ghosh¹, Prajyot Jayadev Nagtilak¹, Manmohan Kapur¹

Affiliation

¹ Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road , Bhauri, Bhopal 462066 , Madhya Pradesh , India.

PMID: 30998382
DOI: 10.1021/acs.orglett.9b00958

Abstract

Allenes are unique coupling partners in transition-metal-catalyzed C-H functionalization leading to a variety of products via alkenylation, allenylation, allylation, and annulation reactions. The outcome is governed by both the reactivity of the allene and the formation and stability of the organometallic intermediate. An efficient Rh(III)-catalyzed, weakly coordinating group-directed dienylation of electronically unbiased allenes is developed using an N-acyl amino acid as a ligand. Further elaboration of the dienylated products to construct polycyclic compounds is also described.

Publication types

Research Support, Non-U.S. Gov't