Results obtained from this study demonstrated that alkyl Petasis boron-Mannich strategy reported herein employs readily available and bench-stable building blocks. This strategy features operational simplicity and enables the rapid and modular preparation of a variety of complex alkyl amies with a high fraction of C(sp 3 ). In addition to providing access to pharmaceutically relevant building blocks, this transformation also revealed a more general Petasis-type coupling of aldehyde, amine, and alkyl boronic acids via a radical process. Consequently, the construction of alkyl amines has showcased remarkable capability of this transformation to rapidly access complex amino-contained derivatives and establish C(sp 3 )-N bonds that were previously challenging.