Yulab

breaking one CH bond per day...keeping headaches away...

[Yulab @YulabJin]

this Pd(II)Pd(0)Pd(II) cycle has much better heterocycle tolerance than Pd(II)Pd(IV) cycle.

[Yulab @YulabJin]

These 41 heterocycles have not been compatible with sp3 CH2 coupling before , the key is the non substituted pyridines, quinolines, Happy July 4, medichem friends!

[Yulab @YulabJin]

Sp3 Methylene CH coupling with heteroaryls has been limited (really annoying for medichemists). With bifunctional pyridone ligands and new mechanism via Pd(II)/Pd(0), we made a big stride: https://t.co/krVnNkj1Y2

[Yulab @YulabJin]

@mynameis_rob @iridium_tea Thanks 🙏

[Yulab @YulabJin]

Unlike functional group conversion, C-H bonds too far or too close are both hard to activate, but it is also the beauty if we can. Piperidine as the top pharmacophore, needs reaction to edit, but C-3 is too close, one bond extension works: Nat. Catal: https://t.co/NHrUU65h9m.

[Yulab @YulabJin]

Sp3CHCoupling typically uses ArI and Ag, a huge drawback for process chemistry. With a long sigh, an unexpected Pd(II)/Pd(0)/Pd(II) cycle avoided both. Again and again, ligand design is the key for advancing CH activation: https://t.co/gFHEGPoH57

[Yulab @YulabJin]

Methylene CH can now be coupled with Aryl CH. The scope is limited, but what new ligand can do is always a pleasant surprise: https://t.co/VvSwyYkMd1

[Yulab @YulabJin]

4+2 via multiple C-H activation and stitching, an alternative disconnection for Diels-Alder and bicyclic scaffolds, Nat. Chem: 10.1038/s41557-026-02077-x

[Yulab @YulabJin]

CH3 on acyclic and cyclic acids has distinct reactivity with latter much less reactive due to ring strain in spiro TS. But if we can activate such CH3, a new disconnection for spiro ring emerges, especially if CH2 can follow, hate and love of CH chem:

https://t.co/o4nmAiLPs1

[Total Synthesis @TotalSynthesis]

#TotalSynthesis of (+)-Melicolone K Enabled by a Late-Stage Programmed C–H Functionalization by Ziqi Jia, Peijie Sun, Tianzhe Wang, Yidian Sheng, Chenlong Zhu, Jun Xuan, and Hanfeng Ding @HanfengD in @J_A_C_S https://t.co/Eqfyx8W7fk

[Yulab @YulabJin]

Another Creative use of our SO2NH directed sp3 CH olefination in complex synthesis, enabling a new disconnection!

[Total Synthesis @TotalSynthesis]

#TotalSynthesis of (+)-Melicolone K Enabled by a Late-Stage Programmed C–H Functionalization by Ziqi Jia, Peijie Sun, Tianzhe Wang, Yidian Sheng, Chenlong Zhu, Jun Xuan, and Hanfeng Ding @HanfengD in @J_A_C_S https://t.co/Eqfyx8W7fk

[Yulab @YulabJin]

@MJKoh87 @scrippsresearch @ChemNUS Great to see the energies of organic chemistry in Singapore 👍

[Yulab @YulabJin]

Inexpensive internal oxidant NHOMe for redox neutral gamma C-H amination, handy for medicinal chemists. Angew Chem ASAP

[Yulab @YulabJin]

@mynameis_rob @guoyuanyang I copied the wrong version in airport will change soon

[Yulab @YulabJin]

Since the first example in 2008, we have reported 44 enantioselective CH activation examples with different classes of substrates, involving coupling, halogenation, oxidation, and cyclization, now enantio-CH triggered rearrangement, a new method for chiral tertiary fluorides.

[Yulab @YulabJin]

@mynameis_rob @guoyuanyang Thanks, will replace

[Yulab @YulabJin]

@MorenRmm Thanks 🙏 once you make a chiral carbon palladium bond, you have unlimited possibilities for making new bonds in various manner !

[Yulab @YulabJin]

@guoyuanyang Thank you for pointing out will make correction !

[Yulab @YulabJin]

@R2G_UCSD Thank you! Expanding enantioselective CH activation to different classes of reactions is important !

[Yulab @YulabJin]

@J_A_C_S Thanks !

[Yulab @YulabJin]

@J_A_C_S Great work !