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Synthesis of isoquinolones

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In rhodium-catalyzed C-H activation/annulation reactions for the synthesis of sixteen 3,4-unsubstituted isoquinolones, vinyl acetate emerges as a convenient acetylene equivalent. The complementary regiochemical preferences of enol ethers versus enol esters/enamides is discussed.
N. J. Webb, S. P. Marsden, S. A. Raw, Org. Lett., 2014, 16, 4716-4721.


N-Chloroamides can be used as a directing synthon for cobalt-catalyzed room-temperature C-H activation. The reaction with alkynes as coupling partner provides isoquinolones, a class of synthetically and pharmaceutically important compounds.
X. Yu, K. Chen, S. Guo, P. Shi, C. Song, J. Zhu, Org. Lett., 2017, 19, 5348-5351.


KOtBu-promoted SNAr reaction of 2-halobenzonitriles with ketones followed by Cu(OAc)2-catalyzed cyclization gives isoquinolone derivatives in good yields.
M. S. Mayo, X. Yu, X. Feng, Y. Yamamoto, M. Bao, J. Org. Chem., 2015, 80, 3998-4002.


The isoquinolone scaffold can be arylated using aryliodonium salts as the coupling partners at either the C4 or C8 position. The C4-selective arylation was successfully achieved via an electrophilic palladation pathway, whereas an Ir(III) catalytic system resulted in C-C bond formation exclusively at the C8 position.
S. Lee, S. Mah, S. Hong, Org. Lett., 2015, 17, 3864-3867.


The isoquinolone scaffold can be arylated using aryliodonium salts as the coupling partners at either the C4 or C8 position. The C4-selective arylation was successfully achieved via an electrophilic palladation pathway, whereas an Ir(III) catalytic system resulted in C-C bond formation exclusively at the C8 position.
S. Lee, S. Mah, S. Hong, Org. Lett., 2015, 17, 3864-3867.


A Rh-catalyzed redox-neutral annulation of primary benzamides with diazo compounds provides isoquinolinones. This efficient and economic procedure exhibited good functional group tolerability, scalability, and regioselectivity, obviating the need for oxidants, and only environmentally benign N2 and H2O were released.
Y. Wu, P. Sun, K. Zhang, T. Yang, H. Yao, A. Lin, J. Org. Chem., 2016, 81, 2166-2173.


A chemoselective ruthenium(II) catalysis enabled mild reaction conditions for positional selective annulations of bromoalkynes to provide isoquinolones with organic substituents distal to nitrogen - complementary to  previous protocols.
H. Huang, S. Nakanowatari, L. Ackermann, Org. Lett., 2017, 19, 4620-4623.


A novel Pd-catalyzed cascade dehydrogenative cross-coupling/annulation reaction of N-alkoxybenzamides with β-keto esters enables the synthesis of isoquinolinone derivatives. A plausible mechanism involves α-C(sp2)-H activation and a Pd(II)/Pd(IV) catalytic cycle.
G.-D. Xu, Z.-Z. Huang, Org. Lett., 2017, 19, 6265-6267.