$$S=\sum_{k=1}^{\infty}\left(\frac{\left(-1\right)^{k-1}}{k+\frac{1}{2}}\ln\left(1-\frac{1}{\left(k+\frac{1}{2}\right)^{2}}\right)\right)$$
Let, $$f(a)=\sum_{k=1}^{\infty}\left(\frac{\left(-1\right)^{k}}{2k+1}\ln\left(2k+a\right)\right)$$ then S can be represented as follows (after expanding everything): $$S=4f(1)-2f(-1)-2f(3)$$
Although I am not sure, but $f(1)$ seems to have a closed form as follows:
$$-\frac{1}{4}\gamma_{1}\left(\frac{3}{4}\right)+\frac{1}{4}\gamma_1\left(\frac{5}{4}\right)+\ln\left(2\right)\left(\frac{\pi}{2}-2\right)$$
where, $\gamma_n$ is the $n$th Stieltjes Constant.
I did get the answer for $f(1)$ without the Stieltjes Consants from one of my friends as follows:
$$-\frac{\pi}{4}\left(\gamma+2\ln2+3\ln\left(\pi\right)-4\ln\left[\Gamma\left(\frac{1}{4}\right)\right]\right)$$
He mentioned it as "Dirichlet Beta Derivative Evaluated at 1".
As a side note, this would imply: $$\gamma_1\left(\frac{5}{4}\right)-\gamma_1\left(\frac{3}{4}\right)=-\pi \gamma-4\pi\ln2-3\pi\ln\left(\pi\right)+4\pi\ln\left[\Gamma\left(\frac{1}{4}\right)\right]+8\ln\left(2\right)$$
I have no idea about $f(-1)$ and $f(3)$.
Also, I have no reason to believe a Closed Form Exists.
Edit: Using another approach as follows:
Using Series Expansion for $\ln(1-x)$ and rearranging the Summation: $$S=\sum_{r=1}^{\infty}\frac{2^{1+2r}}{r}\sum_{k=1}^{\infty}\frac{\left(-1\right)^{k}}{\left(2k+1\right)^{1+2r}}$$
And it seems that: Infinite Series $\sum\limits_{n=0}^\infty\frac{(-1)^n}{(2n+1)^{2m+1}}$ $$\sum_{k=0}^{\infty}\frac{\left(-1\right)^{k}}{\left(2k+1\right)^{1+2r}}=\frac{\left(-1\right)^{r}E_{2r}\pi^{2r+1}}{2^{2r+2}\left(2r\right)!}$$ where, $E_{2r}$ are the Euler Numbers.
$$S=\lim_{\alpha\to\infty}\sum_{r=1}^{\alpha}\frac{2^{1+2r}}{r}\left(\frac{\left(-1\right)^{r}E_{2r}\pi^{2r+1}}{2^{2r+2}\left(2r\right)!}-1\right)$$ Though this probably made it tougher.