TY  - GEN
ID  - heidok30611
CY  - Heidelberg
AV  - public
Y1  - 2022///
TI  - Gold-Catalyzed C-H Alkynylations with Hypervalent Iodine(III) Reagents
N2  - In Chapter 2, a gold-catalyzed direct alkynylation for the synthesis of 1,3-enynes using
alkyl 3-aminoacrylates and hypervalent iodine reagents is reported. This reaction,
which involves the formation of an alkynyl Au(III) species and a direct C-H activation
of alkyl 3-aminoacrylates, reports twenty-six successful conversions in 62-92% yield
with excellent functional group tolerance. In addition, only one configuration of 1,3-
enynes containing enamines is produced and no further cyclization product is found.
In Chapter 3, a gold-catalyzed cascade C(sp3)-H alkynylation/ oxy-alkynylation of ?-
keto compounds with hypervalent iodine(III) reagents for the synthesis of tetrasubstituted
furans is described. The alkynyl Au(III) species plays a crucial role in
Au(I)/Au(III) catalytic cycles. The two operating catalytic cycles include an
alkynylation of activated C(sp3)-H bond and an oxy-alkynylation of an ?-alkynyl ketone.
This simple strategy features mild reaction conditions, high functional group tolerance,
and a wide substrate scope. Furthermore, the synthetic utility of the method was
demonstrated by diverse functionalizations of the final products. Gram-scale synthesis
and proposed mechanism are also presented.
In Chapter 4, another gold-catalyzed cascade C(sp3)?H alkynylation/Nitrogenalkynylation
of 2-pyridine compounds with hypervalent iodine(III) reagents for the
synthesis of poly-substituted indolizines is described. The broad substrate scope, good
functional group tolerance and good efficiency render this method useful for organic
synthesis, especially for the synthesis of nitrogen-containing compounds. Gram-scale
synthesis and proposed mechanism are also revealed.
A1  - Han, Chunyu
UR  - https://archiv.ub.uni-heidelberg.de/volltextserver/30611/
ER  -