Catalyst-enabled Site-selectivity in the Iridium-catalyzed C–H Borylation of Arenes

Abstract

Yusuke Kuroda was born and raised in Osaka, Japan. He obtained his B.S. degree from Kyoto University under the supervision of Profs. Yoshiji Takemoto and Kiyosei Takasu in 2011. He then joined the Takasu group to purse his Ph.D. where he mainly worked on organocatalysis. After obtaining his Ph.D. degree under the supervision of Profs. Kiyosei Takasu and Kenichi Yamada in 2016, he then undertook postdoctoral studies with Prof.

Iridium‐Catalysed C−H Borylation of Heteroarenes: Balancing Steric and Electronic Regiocontrol

“…A comprehensive discussion of these is beyond the scope of this article and the interested reader is directed to more specialised reviews. [65][66][67] For example, it is possible to use groups within the coordination sphere of the Ir complex to direct the borylation via chelation control. This may be achieved using both inner-sphere and outer-sphere directed processes ( Figure 3).…”

“…[60] This is attributed to the enhanced acidity of these C À H bonds and relates to the intrinsic selectivity observed in many heterocyclic systems discussed below.Reflecting these observations,amajor challenge in CÀHb orylation has been to develop methodologies that afford good levels of control in sterically uncongested substrates,a nd an umber of elegant strategies have been reported which accomplish this.A comprehensive discussion of these is beyond the scope of this article and the interested reader is directed to more specialised reviews. [65][66][67] Fore xample,i ti sp ossible to use groups within the coordination sphere of the Ir complex to direct the borylation via chelation control. This may be achieved using both inner-sphere and outer-sphere directed processes ( Figure 3).…”

Iridium‐katalysierte C‐H‐Borylierung von Heteroarenen: Eine Balance zwischen sterischer and elektronischer Regiokontrolle

“…Aufgrund dieser Beobachtungen ist eine der größten Herausforderungen der C‐H‐Borylierung die Entwicklung von Methoden, die ein hohes Niveau an Kontrolle in sterisch ungehinderten Substraten garantieren. Eine Vielzahl eleganter Beispiele wurde veröffentlicht, in denen dies gelang, jedoch ist eine umfassende Diskussion außerhalb des Rahmens dieses Aufsatzes, und der interessierte Leser sei auf spezialisiertere Aufsätze verwiesen [65–67] . Es ist zum Beispiel möglich, Gruppen innerhalb der Koordinationssphäre des Ir‐Komlexes zu nutzen, um die Borylierung durch Chelatbildung zu steuern.…”

Electronically Driven Regioselective Iridium‐Catalyzed C−H Borylation of Donor‐π‐Acceptor Chromophores Containing Triarylboron Acceptors

“…This catalytic system has been thoroughly investigated and exhibits a high regioselectivity due to the sterically bulky nature of the proposed catalytically active species . Additionally, the regioselectivity can also be influenced by functional groups or by modification of the ligand .…”