Site-Selective Functionalization of Unactivated Allylic C–H Bonds via Direct Deprotonation with KTMP: Application to the Formal Total Synthesis of (+)-Artemisinin from Amorphadiene
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DOI: 10.1021/acs.orglett.2c04145
Abstract: The site-selective functionalization of unactivated allylic C–H bonds via direct deprotonation using KTMP is described. The conversion of amorphadiene to artemisinic alcohol via a simple, highly regioselective deprotonation over 4 other possible allylic sites is… read more here.
Keywords: functionalization unactivated; site selective; allylic bonds; selective functionalization ... See more keywords
Rhodium-Catalyzed Allylic C-H Functionalization of Unactivated Alkenes with α-Diazocarbonyl Compounds.
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DOI: 10.1021/acs.orglett.2c04356
Abstract: A redox-neutral mild methodology for the allylic C-H alkylation of unactivated alkenes with diazo compounds is demonstrated. The developed protocol is able to bypass the possibility of the cyclopropanation of an alkene upon its reaction… read more here.
Keywords: functionalization unactivated; alkenes diazocarbonyl; catalyzed allylic; rhodium catalyzed ... See more keywords
Electrochemically Promoted Fluoroalkylation-Distal Functionalization of Unactivated Alkenes.
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DOI: 10.1021/acs.orglett.9b00444
Abstract: Difunctionalization of olefins represents a powerful synthetic tool and yet a challenging task. This work describes an electrochemically enabled fluoroalkylation-migration reaction of unactivated olefins in the absence of a strong oxidant or heavy metal catalyst,… read more here.
Keywords: fluoroalkylation; fluoroalkylation distal; distal functionalization; functionalization unactivated ... See more keywords
Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp3 C–O Bonds in Cyclic Acetals
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DOI: 10.1021/jacs.2c04513
Abstract: A dual catalytic manifold that enables site-selective functionalization of unactivated sp3 C–O bonds in cyclic acetals with aryl and alkyl halides is reported. The reaction is triggered by an appropriate σ*–p orbital overlap prior to… read more here.
Keywords: functionalization unactivated; unactivated sp3; site selective; sp3 bonds ... See more keywords
Controllable access to trifluoromethyl-containing indoles and indolines: palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides
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DOI: 10.1039/d2sc00546h
Abstract: The synthesis of diverse products from the same starting materials is always attractive in organic chemistry. Here, a palladium-catalyzed substrate-controlled regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides has been developed, which provides a direct… read more here.
Keywords: functionalization unactivated; alkenes trifluoroacetimidoyl; palladium catalyzed; trifluoroacetimidoyl chlorides ... See more keywords